Conjugated nitrile derivative, liquid crystal composition, and liquid crystal display elements

ABSTRACT

Liquid crystalline compounds having a wide temperature range of liquid crystal phase, a high dielectric anisotropy, and a high optical anisotropy; and liquid crystal compositions and display devices containing the composition. The liquid crystalline compounds are conjugated nitrile derivatives expressed by the formula (1) ##STR1## wherein R represents an alkyl group or a fluoroalkyl group each having 1 to 10 carbon atoms, halogen atom, or cyano group provided that in the alkyl or fluoroalkyl group, one or not-adjacent two or more methylene or fluoromethylene groups may be replaced by oxygen atom or 1,2-ethenylene group; A 1 , A 2 , A 3  and A 4  represent 1,4-cyclohexylene group, 1,4-phenylene in which one or two hydrogen atoms on the ring may be replaced by fluorine atom, 1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; B 1 , B 2 , and B 3  independently represent a covalent bond, 1,2-ethylene group, 1,2-ethenylene group, 1,2-ethynylene group, carbonyloxy group, methylenoxy group, or 1,4-butylene group; m, n, and p are 0 or 1; and G represents a group expressed by the formula ##STR2##

This application is a 371 application of International Application No.PCT/JP97/04328 filed Nov. 27, 1997.

TECHNICAL FIELD

The present invention relates to liquid crystalline compounds and liquidcrystal compositions. More specifically, the invention relates toconjugated nitrile derivatives of liquid crystalline compoundspreferable as component of liquid crystal compositions; liquid crystalcompositions comprising the nitrile derivative; and liquid crystaldisplay devices fabricated by using the liquid crystal composition.

BACKGROUND ART

Liquid crystal display devices utilize optical (refractive) anisotropyand dielectric anisotropy of liquid crystalline compounds. Viewing fromthe aspect of display mode, display devices of twisted nematic (TN)type, super twisted nematic (STN) type, dynamic scattering (DS) type,guest,host (GH) type, or DAP type organized according to theirelectrooptical effect are known. From the aspect of driving mode,display devices of static driving mode, time shearing addressing mode,active matrix driving mode, or two-frequency addressing scheme areknown. Liquid crystal substances used for the display devices arerequired to exhibit a liquid crystal phase in a wide temperature rangeand to be stable against heat, light, moisture, air, electric field, andelectromagnetic radiation.

However, since it is impossible to satisfy all of such requirements by asingle compound at present, it is a current situation that several, orin some cases more than twenty liquid crystalline compounds are mixedand used as liquid crystal compositions. Accordingly, the liquidcrystalline compounds have come to be required to exhibit excellentmiscibility each other. Recently in particular, since display devicesare used in many instances in sever environments such as at cryogenictemperatures, improvement of the compounds in the miscibility at lowtemperatures has come to be required.

With the increase of demand for display devices of high quality,requests for liquid crystal composition having an improved responsespeed to the change in electric field, and steepness have beenincreased. In order to fulfil the requirements, it is required to useliquid crystal materials having a low viscosity and a large dielectricanisotropy value as component of liquid crystal compositions.

In order to increase the response speed of liquid crystal compositions,it is effective to make the thickness (d) of liquid crystal cells small(thin) in addition to satisfying the requirements described above. Inthis case, however, it is necessary to increase optical anisotropy value(Δn) (to use liquid crystalline compounds having a large Δn ascomponent) for the reason described below. That is, excellent displaycontrast and wide visual angle are found as other characteristicsrequired of display devices. In order to achieve this end, it isnecessary to maintain the product of Δn and d (Δn·d) at a certain value,and thus, when d is made small according to the measures describedabove, it is necessary to increase Δn.

For originating liquid crystalline compounds having a large Δn, it issufficient, for instance, to introduce ethynylene group into a liquidcrystal molecule, and it is known by means of the compounds expressed bythe formula (13) (Japanese Patent Publication No. Hei 3-29051) andcompounds expressed by one of the formulas (14) to (16) (DE 4027458 andWO 90-13610) that the compounds can be changed into ones having a largevalue even in dielectric anisotropy (Δε) by altering the ethynylenegroup into the one having an electron attractive group, for example, CN,Cl, CHF₂, or CF₃ as substituent. ##STR3## wherein R represents an alkylgroup.

However, as to the compounds expressed by the formula (13), theirelectric properties are not disclosed at all in the Japanese PatentPublication No. Hei 3-29051. Compounds expressed by one of the formulas(14) to (16) are narrow in the temperature range of liquid crystalphase, and they can not be said to exhibit a sufficiently large value ofeither Δn and Δε besides.

An object of the present invention is to solve the defects in theconventional technology. Another object of the present invention is toprovide conjugated nitrile derivatives, novel liquid crystallinecompounds having a sufficiently large Δn and a large Δε, being excellentin miscibility with other liquid crystalline compounds, having a lowviscosity, and being chemically and physically stable; to provide liquidcrystal compositions comprising the nitrile derivative; and to provideliquid crystal display devices fabricated by using the liquid crystalcomposition.

DISCLOSURE OF THE INVENTION

As a result of diligent investigations by the present inventors toachieve the objects described above, compounds of a novel structurehaving improved characteristics compared with known liquid crystallinecompounds have been found, leading to the accomplishment of the presentinvention.

Summary of the present invention is as follows:

(1) A conjugated nitrile derivative expressed by the general formula (1)##STR4## wherein rings A₁, A₂, A₃, and A₄ independently represent1,4-cyclohexylene, 1,4-phenylene in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom, 1,3-dioxane-2,5-diyl, orpyrimidine-2,5-diyl; B₁, B₂, and B₃ independently pepresent a covalentbond, 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene,methylenoxy, carbonyloxy, or 1,4-butylene group; G represents theformula (2), (3), or (4) ##STR5## R represents an alkyl group having 1to 10 carbon atoms, a fluoroalkyl group having 1 to 10 carbon atoms, ahalogen atom, or cyano group provided that in the alkyl group orfluoroalkyl group, one or not-adjacent two or more methylene groups orfluoromethylene groups may be replaced by oxygen atom or 1,2-ethenylenegroup; m, n, and p are independently 0 or 1; and each element whichconstitutes the compound may be selected from its isotopes.

(2) The conjugated nitrile derivative recited in paragraph (1) abovewherein m=n=p=0.

(3) The conjugated nitrile derivative recited in paragraph (1) abovewherein m=n=0, and p=1.

(4) The conjugated nitrile derivative recited in paragraph (1) abovewherein m=0, and n=p=1.

(5) The conjugated nitrile derivative recited in paragraph (1) abovewherein m=n=p=1.

(6) The conjugated nitrile derivative recited in paragraph (3) abovewherein G is the group expressed by the formula (2).

(7) The conjugated nitrile derivative recited in paragraph (6) abovewherein A₄ is 1,4-cyclohexylene.

(8) The conjugated nitrile derivative recited in paragraph (6) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(9) The conjugated nitrile derivative recited in paragraph (7) abovewherein A₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.

(10) The conjugated nitrile derivative recited in paragraph (3) abovewherein G is the group expressed by the formula (3).

(11) The conjugated nitrile derivative recited in paragraph (10) abovewherein A₄ is 1,4-cyclohexylene.

(12) The conjugated nitrile derivative recited in paragraph (10) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(13) The conjugated nitrile derivative recited in paragraph (11) abovewherein A₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.

(14) The conjugated nitrile derivative recited in paragraph (12) abovewherein A₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.

(15) The conjugated nitrile derivative recited in paragraph (3) abovewherein G is the group expressed by the formula (4).

(16) The conjugated nitrile derivative recited in paragraph (15) abovewherein A₄ is 1,4-cyclohexylene.

(17) The conjugated nitrile derivative recited in paragraph (15) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(18) The conjugated nitrile derivative recited in paragraph (16) abovewherein A₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.

(19) The conjugated nitrile derivative recited in paragraph (17) abovewherein A₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.

(20) The conjugated nitrile derivative recited in paragraph (4) abovewherein G is the group expressed by the formula (2).

(21) The conjugated nitrile derivative recited in paragraph (20) abovewherein A₄ is 1,4-cyclohexylene.

(22) The conjugated nitrile derivative recited in paragraph (20) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(23) The conjugated nitrile derivative recited in paragraph (4) abovewherein G is the group expressed by the formula (3).

(24) The conjugated nitrile derivative recited in paragraph (23) abovewherein A₄ is 1,4-cyclohexylene.

(25) The conjugated nitrile derivative recited in paragraph (23) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(26) The conjugated nitrile derivative recited in paragraph (4) abovewherein G is the group expressed by the formula (4).

(27) The conjugated nitrile derivative recited in paragraph (26) abovewherein A₄ is 1,4-cyclohexylene.

(28) The conjugated nitrile derivative recited in paragraph (26) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(29) The conjugated nitrile derivative recited in paragraph (5) whereinG is the group expressed by the formula (2).

(30) The conjugated nitrile derivative recited in paragraph (29) abovewherein A₄ is 1,4-cyclohexylene.

(31) The conjugated nitrile derivative recited in paragraph (29) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(32) The conjugated nitrile derivative recited in paragraph (5) abovewherein G is the group expressed by the formula (3).

(33) The conjugated nitrile derivative recited in paragraph (32) abovewherein A₄ is 1,4-cyclohexylene.

(34) The conjugated nitrile derivative recited in paragraph (32) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(35) The conjugated nitrile derivative recited in paragraph (5) abovewherein G is the group expressed by the formula (4).

(36) The conjugated nitrile derivative recited in paragraph (35) abovewherein A₄ is 1,4-cyclohexylene.

(37) The conjugated nitrile derivative recited in paragraph (35) abovewherein A₄ is 1,4-phenylene ring in which one or two hydrogen atoms onthe ring may be replaced by fluorine atom.

(38) A liquid crystal composition comprising at least one conjugatednitrile derivative recited in any one of paragraphs (1) through (37)above.

(39) A liquid crystal composition, comprising, as a first component, atleast one conjugated nitrile derivative recited in any one of paragraphs(1) through (37) above, and comprising, as a second component, at leastone compound selected from the group consisting of the compoundsexpressed by any one of the general formulas (5), (6), and (7) ##STR6##wherein R₃, Y₁, L₁, L₂, Z₁, and Z₂ may be the same or different from oneanother among the formulas; R₃ represents an alkyl group having 1 to 10carbon atoms in which alkyl group, one or not-adjacent two or moremethylene groups may be replaced by oxygen atom or --CH═CH--, and anyhydrogen atom may be replaced by fluorine atom; Y₁ represents fluorineatom, chlorine atom, OCF₃, OCF₂ H, CF₃, CF₂ H, CFH₂, OCF₂ CF₂ H, or OCF₂CFHCF₃ ; L₁ and L₂ independently represent hydrogen atom or fluorineatom; Z₁ and Z₂ independently represent 1,2-ethylene group, 1,4-butylenegroup, --COO--, --CF₂ O--, --OCF₂ --, --CH═CH--, or a covalent bond;ring B represents trans-1,4-cyclohexylene or 1,3-dioxane-2,5-diyl, or1,4-phenylene in which hydrogen atom on the ring may be replaced byfluorine atom; ring C represents trans-1,4-cyclohexylene, or1,4-phenylene in which hydrogen atom on the ring may be replaced byfluorine atom; and each element which constitutes the compounds of eachof the general formulas may be selected from its isotopes.

(40) A liquid crystal composition, comprising, as a first component, atleast one conjugated nitrile derivative recited in any one of paragraphs(1) through (37) above, and comprising, as a second component, at leastone compound selected from the group consisting of the compoundsexpressed by the general formula (8) or (9) ##STR7## wherein R₄ and R₅independently represent an alkyl group having 1 to 10 carbon atoms inwhich alkyl group, one or not-adjacent two or more methylene groups maybe replaced by oxygen atom or --CH═CH--, and any hydrogen atom may bereplaced by fluorine atom; Y₂ represents --CN group or --C.tbd.C--CN;ring E represents trans-1,4-cyclohexylene, 1,4-phenylene,1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; ring G representstrans-1,4-cyclohexylene, 1,4-phenylene in which hydrogen atom on thering may be replaced by fluorine atom, or pyrimidine-2,5-diyl; ring Hrepresents trans-1,4-cyclohexylene or 1,4-phenylene; Z₃ represents1,2-ethylene group, --COO--, or a covalent bond; L₃, L₄, and L₅independently represent hydrogen atom or fluorine atom; b, c, and d areindependently 0 or 1; and each element which constitutes the compoundsof each of the general formulas may be selected from its isotopes.

(41) A liquid crystal composition, comprising, as a first component, atleast one conjugated nitrile derivative recited in any one of paragraphs(1) through (37) above, comprising, as a second component, at least onecompound selected from the group consisting of the compounds expressedby any one of the general formulas (5), (6), and (7) described above,and comprising, as a third component, at least one compound selectedfrom the group consisting of the compounds expressed by any one of thegeneral formulas (10), (11), and (12) ##STR8## wherein R₆, R₇, I, J, andK may be the same or different from one another among the formulas; R₆and R₇ independently represent an alkyl group having 1 to 10 carbonatoms in which alkyl group, one or not-adjacent two or more methylenegroups may be replaced by oxygen atom or --CH═CH--, and any hydrogenatom may be replaced by fluorine atom; I, J, and K independentlyrepresent trans-1,4-cyclohexylene or pyrimidine-2,5-diyl, or1,4-phenylene in which hydrogen atom on the ring may be replaced byfluorine atom; Z₄ and Z₅ independently represent --C.tbd.C--, --COO--,--CH₂ CH₂ --, --CH═CH--, or a covalent bond; and each element whichconstitutes the compounds of each of the general formulas may beselected from its isotopes.

(42) A liquid crystal composition, comprising, as a first component, atleast one conjugated nitrile derivative recited in any one of paragraphs(1) through (37) above, comprising, as a second component, at least onecompound selected from the group consisting of the compounds expressedby the general formula (8) or (9) described above, and comprising, as athird component, at least one compound selected from the groupconsisting of the compounds expressed by any one of the general formulas(10), (11), and (12) described above.

(43) A liquid crystal composition, comprising, as a first component, atleast one conjugated nitrile derivative recited in any one of paragraphs(1) through (37) above, comprising, as a part of a second component, atleast one compound selected from the group consisting of the compoundsexpressed by any one of the general formulas (5), (6), and (7) describedabove, comprising, as another part of the second component, at least onecompound selected from the group consisting of the compounds expressedby the general formula (8) or (9) described above, and comprising, as athird component, at least one compound selected from the groupconsisting of the compounds expressed by any one of the general formulas(10), (11), and (12) described above.

(44) A liquid crystal composition recited in any one of paragraphs (38)to (43) above wherein the liquid crystal composition further comprisesan optically active compound.

(45) A liquid crystal display device fabricated by using the liquidcrystal composition recited in any one of paragraphs (38) to (44) above.

As described above, the conjugated nitrile derivatives, the liquidcrystalline compounds of the present invention are expressed by thegeneral formula (1). Among them, a group of the compounds expressed byone of the formulas (1-a) to (1-n) can particularly be mentioned aspreferable examples. ##STR9## wherein R and G have the same meaning asdescribed above.

Any of these compounds of the present invention exhibit a large Δn.Besides, they are low in viscosity, excellent in miscibility with otherliquid crystalline compounds, and chemically and physically stable.Since particularly the compounds expressed by one of the formulas (1-k)to (1-n) further have a high clearing point, they can be used ascomponent when liquid crystal compositions having a high upper limittemperature of liquid crystal are produced.

Since the compounds expressed by one of the formulas (1-e) to (1-n),particularly the compounds expressed by the formula (1-e), (1-j), (1-k),(1-l), or (1-m) have an extremely large Δn, they are remarkably useful.

All liquid crystalline compounds of the present invention expressed bythe general formula (1) do not necessarily exhibit a liquid crystalphase. However, since any of the compounds is excellent in miscibilitywith other liquid crystalline compounds, and does not considerably loweror narrow the temperature range of nematic phase of other liquidcrystalline compounds when mixed with them, it is useful as component ofliquid crystal compositions even if it does not exhibit a liquid crystalphase by itself.

Liquid crystal compositions of the present invention comprise, as afirst component, at least one liquid crystalline compound expressed bythe general formula (1).

It is necessary to develop excellent characteristics that the content ofthe compound is 0.1 to 99.9% by weight based on the amount of the liquidcrystal composition.

While the liquid crystal compositions of the present invention may becomposed only of the first component described above, compositions inwhich at least one compound selected from the group consisting of thecompounds expressed by one of the general formulas (5), (6), and (7)described above (the compounds are hereinafter referred to as secondcomponent A) and/or at least one compound selected from the groupconsisting of the compounds expressed by the general formula (8) or (9)described above (the compounds are hereinafter referred to as secondcomponent B) are mixed as a second component in addition to the firstcomponent; or compositions in which at least one compound selected fromthe group consisting of the compounds expressed by one of the generalformulas (10), (11), and (12) described above are additionally mixed asa third component to the first and second components are preferable.Further, an optically active compound, and known compounds for thepurpose of adjusting threshold voltage, temperature range of liquidcrystal phase, Δn, Δε, and viscosity can be mixed as other components tothe compositions.

Among the second component A, compounds expressed by one of the formulas(5-1) to (5-9) can be mentioned as preferable examples of the compoundsincluded in the general formula (5), compounds expressed by one of theformulas (6-1) to (6-69) can be mentioned as preferable examples of thecompounds included in the general formula (6), and compounds expressedby one of the formulas (7-1) to (7-24) can be mentioned as preferableexamples of the compounds included in the general formula (7),respectively. ##STR10## wherein R₃ and Y₁ have the same meaning asdescribed above.

Any compounds expressed by one of these general formulas (5) to (7)exhibit a positive Δε, are considerably excellent in thermal stabilityand chemical stability, and are indispensable when liquid crystalcompositions for TFT (AM-LCD) of which a high reliability such as a highvoltage holding ratio (large specific resistivity) is required.

The amount of the compound to be used is suitably in the range of 1 to99.9% by weight based on the total amount of liquid crystal compositionwhen liquid crystal compositions for TFT are produced, and the amount ispreferably 10 to 97% by weight, and more desirably 40 to 95% by weight.In that case, the compositions may further comprise a compound expressedby one of the general formulas (10) to (12) for the purpose of adjustingviscosity.

Compounds expressed by one of the general formulas (5) to (7) can beused when liquid crystal compositions for STN display mode or TN displaymode are produced. However, since the compounds are relatively low inthe effect of lowering threshold voltage of liquid crystal compositions,their amount to be used is preferably less than 50% by weight based onthe total amount of liquid crystal composition.

Next, among the second component B, compounds expressed by one of theformulas (8-1) to (8-40) can be mentioned as preferable examples of thecompounds included in the general formula (8), and compounds expressedby one of the formulas (9-1) to (9-3) can be mentioned as preferableexamples of the compounds included in the general formula (9),respectively. ##STR11## wherein R₄, Y₂, and R₅ have the same meaning asdescribed above.

Compounds expressed by one of these general formula (8) or (9) have apositive and large dielectric anisotropy value Δε, and used particularlyfor the purpose of lowering threshold voltage of liquid crystalcompositions.

Also, they are used for the purpose of improving the steepness of liquidcrystal compositions for STN display mode or TN display mode, includingfor the purpose of adjusting Δn, and widening nematic range such asraising clearing point, and thus they are indispensable compounds whenliquid crystal compositions for STN display mode or TN display mode areproduced.

As the amount of the compounds to be used is increased, thresholdvoltage of liquid crystal compositions can be lowered, but on the otherhand, viscosity is increased. Accordingly, it is advantageous, for lowvoltage driving, to use a large amount of the compound so far asviscosity of liquid crystal compositions satisfies a requiredcharacteristic.

According to such circumstances, when liquid crystal compositions forSTN display mode or TN display mode are produced, the amount of thecompounds to be used is suitably in the range of 0.1 to 99.9% by weightbased on the total amount of liquid crystal composition, and the amountis preferably 10 to 97% by weight and more desirably 40 to 95% byweight.

Among the third component described above, compounds expressed by one ofthe formula (10-1) to (10-11) can be mentioned as preferable examples ofthe compounds included in the general formula (10), compounds expressedby one of the formulas (11-1) to (11-18) can be mentioned as preferableexamples of the compounds included in the general formula (11), andcompounds expressed by one of the formulas (12-1) to (12-6) can bementioned as preferable examples of the compounds included in thegeneral formula (12), respectively. ##STR12## wherein R₆ and R₇ have thesame meaning as described above.

Any compound expressed by one of these general formulas (10) to (12) hasa small absolute value of dielectric anisotropy Δε. Among them,compounds of the general formula (10) are used principally for thepurpose of adjusting viscosity or adjusting Δn of liquid crystalcompositions, and the compounds of the general formula (11) or (12) areused for the purpose of widening nematic range such as raising clearingpoint, and for the purpose of adjusting Δn.

With the increase of the amount to be used, this compound raisesthreshold voltage of liquid crystal compositions, but on the other hand,reduces viscosity. Accordingly, it is desirable to use a large amount ofthe compound so far as threshold voltage of liquid crystal compositionssatisfies a required value.

According to such circumstances, when liquid crystal compositions forTFT are produced, the amount of the compound to be used is suitably lessthan 40% by weight based on the total amount of liquid crystalcomposition, and preferably less than 35% by weight.

On the other hand, when liquid crystal compositions for STN display modeor TN display mode are produced, the amount of the compound to be usedis suitably less than 70% by weight, and preferably less than 60% byweight.

With the exception of such specific cases as liquid crystal compositionsfor OCB (Optically Compensated Birefringence) mode, an optically activecompound, among the other components, is usually added to the liquidcrystal compositions for the purpose of inducing helical structure ofliquid crystal composition to adjust required twist angle and to preventreverse twist.

While the optically active compound is selected from a wide range ofknown compounds, the optically active compound expressed by one of thefollowing formulas (Op-1) to (Op-8) can preferably be mentioned:##STR13##

By the addition of these optically active compounds, the pitch length oftwist of liquid crystal compositions are adjusted. The pitch length oftwist is preferably adjusted in the range of 40 to 200 μm in the case ofliquid crystal compositions for TFT or TN, and preferably adjusted inthe range of 6 to 20 μm in the case of liquid crystal compositions forSTN. In the case for bistable TN mode, it is preferable to adjust thepitch length in the range of 1.5 to 4 μm. In such cases, two or morekind of optically active compounds may be added for the purpose ofadjusting the dependency of the pitch length on temperature.

Liquid crystal compositions provided according to the present inventioncan be produced by methods which are conventional by themselves. Forinstance, the liquid crystal compositions are usually produced by amethod in which various components are dissolved in one another at ahigh temperature.

Further, the liquid crystal compositions of the present invention can beused as ones for guest-host (GH) mode by adding a dichroic dye such asmerocyanine type, styryl type, azo type, azomethine type, azoxy type,quinophthalone type, anthraquinone type, and tetrazine type thereto.Alternatively, the liquid crystal compositions of the present inventioncan be used as NCAP which is prepared by the microencapsulation of anematic liquid crystal, or as liquid crystal compositions for polymerdispersed liquid crystal display devices (PDLCD) represented by polymernet work liquid crystal display devices (PNLCD) prepared by forming apolymer of three-dimensional reticulated structure in a liquid crystal.Still further, the liquid crystal compositions of the present inventioncan be used as ones for electrically controlled birefringence (ECB) modeor dynamic scattering (DS) mode.

While the liquid crystal compositions of the present invention areproduced by such methods as described above, the following CompositionExamples 1 to 46 can be mentioned as their examples:

In each of the Composition Examples, compounds are designated by makinga particular group or structure shown in the column of left sideterminal group, bonding group, ring structure, or right side terminalgroup in Table 1 below correspond to the symbol shown in the same lineand the same column. Designation in the case where the hydrogen atom ontrans-1,4-cyclohexylene and trans,trans-bicyclohexane-4,4'-diyl group isreplaced by its isotope, heavy hydrogen (deuterium) atom is shown bysymbol [1D,˜8D] after excerpting only substituted heavy hydrogen atoms,when both of the groups mentioned above are assumed to be expressed bythe formula (60) and (61), respectively, and any one of hydrogen atomsL¹, L², L³, L⁴, L⁵, L⁶, L⁷, and L⁸ on the ring is assumed to be replacedby one of heavy hydrogen atoms 1D, 2D, 3D, 4D, 5D, 6D, 7D, and 8D.

Compound No. appended to the compounds of the present invention in thefollowing Composition Examples means that the compounds are the same asthose shown in Examples described below and having the same appendedCompound No.; and the content of compounds means % by weight unlessotherwise specified.

Further, data of characteristics in Composition Examples are indicatedby T_(NI) (phase transition temperature of nematic phase-isotropicliquid, or clearing point), T_(MP) (crystallization temperature), η(viscosity: determined at 20.0° C.), An (optical anisotropy value:determined at 25.0° C.), Δε (dielectric anisotropy value: determined at25.0° C.), V_(th) (threshold voltage: determined at 25.0° C.), and P(pitch: determined at 25.0° C.). ##STR14##

                  TABLE 1                                                         ______________________________________                                        Method for Designating Compounds by Using Symbols                             R-(A.sub.1)-Z.sub.1 - . . . -Z.sub.n -(A.sub.n)-X                             ______________________________________                                        1) Left side terminal group R-                                                                      Symbol                                                  ______________________________________                                        C.sub.n H.sub.2n+1 -- n-                                                      C.sub.n H.sub.2n+1 O--                                                                              nO--                                                    C.sub.n H.sub.2n+1 OC.sub.m H.sub.2m --                                                             nOm-                                                    CH.sub.2 ═CH--    V--                                                     CH.sub.2 ═CHC.sub.n H.sub.2n --                                                                 Vn-                                                     C.sub.n H.sub.2n+1 CH═CHC.sub.m H.sub.2m --                                                     nVm-                                                    C.sub.n H.sub.2n+1 CH═CHC.sub.m H.sub.2m CH═CHC.sub.k H.sub.2k                              nVmVk-                                                  F--                   F--                                                     NC--                  C--                                                     FC.sub.n H.sub.2n --  Fn-                                                     FF--C.sub.n H.sub.2n-1 --                                                                           FFn-                                                    ______________________________________                                        2) Ring structure -(A.sub.1)-, -(A.sub.n)-                                                          Symbol                                                  ______________________________________                                                              B                                                        ##STR15##            B(F)                                                     ##STR16##            B(2F, 3F)                                                ##STR17##            B(F, F)                                                  ##STR18##            H                                                        ##STR19##            Py                                                       ##STR20##            G                                                        ##STR21##            Ch                                                      ______________________________________                                        3) Bonding group -Z.sub.1 -, -Z.sub.n -                                                             Symbol                                                  ______________________________________                                        --C.sub.2 H.sub.4 --  2                                                       --C.sub.4 H.sub.8 --  4                                                       --COO--               E                                                       --C.tbd.C--           T                                                       --CH=CH--             V                                                       --CF.sub.2 O--        CF2O                                                    --OCF.sub.2 --        OCF2                                                    ______________________________________                                        4) Right side terminal group -X                                                                     Symbol                                                  ______________________________________                                        --F                   --F                                                     --Cl                  --CL                                                    --CN                  --C                                                     --CF.sub.3            --CF3                                                   --OCF.sub.3           --OCF3                                                  --OCF.sub.2 H         --OCF2H                                                 --OCF.sub.2 CF.sub.2 H                                                                              --OCF2CF2H                                              --C.sub.n H.sub.2n+1                                                          --OC.sub.n H.sub.2n+1 --On                                                    --COOCH.sub.3                                                                 EMe                                                                           --C.sub.n H.sub.2n CH═CH.sub.2                                            nV                                                                            --C.sub.m H.sub.2m CH═CHC.sub.n H.sub.2n+1                                mVn                                                                           --C.sub.m H.sub.2m CH═CHC.sub.n H.sub.2n F                                mVnF                                                                          --CH═CF.sub.2     --VFF                                                   --C.sub.n H.sub.2n CH═CF.sub.2                                            nVFF                                                                          --C.tbd.C--CN                                                                 TC                                                                            --C.tbd.C--CH═CH--CN                                                      TVC                                                                           --CH═CH--C.tbd.C--CN                                                                            --VTC                                                   --C.tbd.C--C.tbd.C--CN                                                        TTC                                                                           ______________________________________                                        5) Example of designation                                                                           Symbol                                                  ______________________________________                                        Example 1             3-H2B(F, F)B(F)--F                                       ##STR22##                                                                    Example 2             3-HB(F)TB-2                                              ##STR23##                                                                    Example 3             1V2-BEB(F, F)--C                                         ##STR24##                                                                    ______________________________________                                    

COMPOSITION EXAMPLE 1

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB-TTC (No. 62)                                                                              10.0%                                                        1V2-BEB(F,F)-C   5.0%                                                         3-HB-C           15.0%                                                        1-BTB-3          5.0%                                                         2-BTB-1          10.0%                                                        3-HH-4           11.0%                                                        3-HHB-1          11.0%                                                        3-HHB-3          9.0%                                                         3-H2BTB-2        4.0%                                                         3-H2BTB-3        4.0%                                                         3-H2BTB-4        4.0%                                                         3-HB(F)TB-2      6.0%                                                         3-HB(F)TB-3      6.0%                                                         ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =104.7° C.

η=14.6 mPa·s

εn=0.190

Δε=7.0

V_(th) =2.21 V.

Further, 0.8 part by weight of the optically active compound expressedby the formula (Op-4) was added to 100 parts by weight of the primaryliquid crystal composition described above to obtain a secondary liquidcrystal composition, and a characteristic of the secondary compositionwas determined to be as follows:

P=11.2 μm.

COMPOSITION EXAMPLE 2

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        5-HH-VTC (No. 34) 5.0%                                                        V2-HB-C           12.0%                                                       1V2-HB-C          12.0%                                                       3-HB-C            10.0%                                                       3-H[1D,2D,3D]B-C  9.0%                                                        3-HB(F)-C         5.0%                                                        2-BTB-1           2.0%                                                        3-HH-4            8.0%                                                        3-HH-VFF          6.0%                                                        2-H[1D,2D,3D]HB-C 3.0%                                                        3-HHB-C           6.0%                                                        3-HB(F)TB-2       8.0%                                                        3-H2BTB-2         5.0%                                                        3-H2BTB-3         5.0%                                                        3-H2BTB-4         4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =95.0° C.

η=18.1 mPa·s

Δn=0.158

Δε=8.5

V_(th) =2.14 V.

COMPOSITION EXAMPLE 3

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HH-TTC (No. 58)                                                                              5.0%                                                         V-HB-TTC (No. 64)                                                                              5.0%                                                         3O1-BEB(F)-C     10.0%                                                        4O1-BEB(F)-C     13.0%                                                        5O1-BEB(F)-C     13.0%                                                        2-HHB(F)-C       15.0%                                                        3-HHB(F)-C       15.0%                                                        3-HB(F)TB-2      4.0%                                                         3-HB(F)TB-3      4.0%                                                         3-HB(F)TB-4      4.0%                                                         3-HHB-1          8.0%                                                         3-HHB-O1         4.0%                                                         ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =110.4° C.

η=85.5 mPa·s

Δn=0.175

Δε=27.8

V_(th) =1.12 V.

COMPOSITION EXAMPLE 4

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HPy-TTC (No. 67)                                                                              3.0%                                                        5-PyB-F           4.0%                                                        3-PyB(F)-F        4.0%                                                        2-BB-C            5.0%                                                        4-BB-C            4.0%                                                        5-BB-C            5.0%                                                        2-PyB-2           2.0%                                                        3-PyB-2           2.0%                                                        4-PyB-2           2.0%                                                        6-PyB-O5          3.0%                                                        6-PyB-O6          3.0%                                                        6-PyB-O7          3.0%                                                        3-PyBB-F          6.0%                                                        4-PyBB-F          6.0%                                                        5-PyBB-F          6.0%                                                        3-HHB-1           6.0%                                                        3-HHB-3           8.0%                                                        2-H2BTB-2         4.0%                                                        2-H2BTB-3         4.0%                                                        2-H2BTB-4         5.0%                                                        3-H2BTB-2         5.0%                                                        3-H2BTB-3         5.0%                                                        3-H2BTB-4         5.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 5

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HHH-VTC (No. 84)                                                                              3.0%                                                        3-GB-C            10.0%                                                       4-GB-C            10.0%                                                       2-BEB-C           12.0%                                                       3-BEB-C           4.0%                                                        3-PyB(F)-F        6.0%                                                        3-HEB-O4          8.0%                                                        4-HEB-O2          6.0%                                                        5-HEB-O1          6.0%                                                        3-HEB-O2          5.0%                                                        5-HEB-O2          4.0%                                                        5-HEB-5           5.0%                                                        4-HEB-5           5.0%                                                        1O-BEB-2          4.0%                                                        3-HHB-1           3.0%                                                        3-HHEBB-C         3.0%                                                        3-HBEBB-C         3.0%                                                        5-HBEBB-C         3.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 6

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        C-BHH-VTC (No. 89)                                                                              2.0%                                                        3-HB-C            18.0%                                                       7-HB-C            3.0%                                                        1O1-HB-C          10.0%                                                       3-HB(F)-C         10.0%                                                       2-PyB-2           2.0%                                                        3-PyB-2           2.0%                                                        4-PyB-2           2.0%                                                        1O1-HH-3          7.0%                                                        2-BTB-O1          7.0%                                                        3-HHB-1           7.0%                                                        3-HHB-F           4.0%                                                        3-HHB-O1          4.0%                                                        3-HHB-3           6.0%                                                        3-H2BTB-2         3.0%                                                        3-H2BTB-3         3.0%                                                        2-PyBH-3          4.0%                                                        3-PyBH-3          3.0%                                                        3-PyBB-2          3.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 7

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        F-BHH-VTC (No. 90)                                                                              3.0%                                                        2O1-BEB(F)-C      5.0%                                                        3O1-BEB(F)-C      12.0%                                                       5O1-BEB(F)-C      4.0%                                                        1V2-BEB(F,F)-C    10.0%                                                       3-HH-EMe          10.0%                                                       3-HB-O2           18.0%                                                       7-HEB-F           2.0%                                                        3-HHEB-F          2.0%                                                        5-HHEB-F          2.0%                                                        3-HBEB-F          4.0%                                                        2O1-HBEB(F)-C     2.0%                                                        3-HB(F)EB(F)-C    2.0%                                                        3-HBEB(F,F)-C     2.0%                                                        3-HHB-F           4.0%                                                        3-HHB-O1          4.0%                                                        3-HHB-3           10.0%                                                       3-HEBEB-F         2.0%                                                        3-HEBEB-1         2.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 8

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB2B-VTC (No. 121)                                                                             3.0%                                                       5-BEB(F)-C         5.0%                                                       V-HB-C             11.0%                                                      5-PyB-C            6.0%                                                       4-BB-3             11.0%                                                      3-HH-2V            10.0%                                                      5-HH-V             11.0%                                                      V-HHB-1            7.0%                                                       V2-HHB-1           15.0%                                                      3-HHB-1            6.0%                                                       1V2-HBB-2          10.0%                                                      3-HHEBH-3          5.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 9

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HBHB-TTC (N0. 156)                                                                             2.0%                                                       2O1-BEB(F)-C       5.0%                                                       3O1-BEB(F)-C       12.0%                                                      5O1-BEB(F)-C       4.0%                                                       1V2-BEB(F,F)-C     16.0%                                                      3-HB-O2            10.0%                                                      3-HH-4             3.0%                                                       3-HHB-F            3.0%                                                       3-HHB-1            8.0%                                                       3-HHB-O1           4.0%                                                       3-HBEB-F           4.0%                                                       3-HHEB-F           6.0%                                                       5-HHEB-F           6.0%                                                       3-H2BTB-2          4.0%                                                       3-H2BTB-3          4.0%                                                       3-H2BTB-4          4.0%                                                       3-HB(F)TB-2        5.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 10

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HVHB-TTC (No. 151)                                                                             3.0%                                                       2-BEB-C            12.0%                                                      3-BEB-C            4.0%                                                       4-BEB-C            6.0%                                                       3-HB-C             25.0%                                                      3-HEB-O4           12.0%                                                      4-HEB-O2           8.0%                                                       5-HEB-O1           8.0%                                                       3-HEB-O2           6.0%                                                       5-HEB-O2           5.0%                                                       3-HHB-1            7.0%                                                       3-HHB-O1           4.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 11

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HBTB-TTC (No. 174)                                                                             3.0%                                                       2-BEB-C            10.0%                                                      5-BB-C             12.0%                                                      7-BB-C             7.0%                                                       1-BTB-3            7.0%                                                       2-BTB-1            7.0%                                                       1O-BEB-2           10.0%                                                      1O-BEB-5           12.0%                                                      2-HHB-1            4.0%                                                       3-HHB-F            4.0%                                                       3-HHB-1            7.0%                                                       3-HHB-O1           4.0%                                                       3-HHB-3            13.0%                                                      ______________________________________                                    

COMPOSITION EXAMPLE 12

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-GHB-TTC (No. 142)                                                                             2.0%                                                        1V2-BEB(F,F)-C    8.0%                                                        3-HB-C            10.0%                                                       V2V-HB-C          12.0%                                                       V2V-HH-3          19.0%                                                       3-HB-O2           4.0%                                                        3-HHB-1           10.0%                                                       3-HHB-3           15.0%                                                       3-HB(F)TB-2       4.0%                                                        3-HB(F)TB-3       4.0%                                                        3-H2BTB-2         4.0%                                                        3-H2BTB-3         4.0%                                                        3-H2BTB-4         4.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 13

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB-TTC (No. 62)                                                                              5.0%                                                         5-HH-VTC (No. 34)                                                                              5.0%                                                         3-HH-TTC (No. 59)                                                                              5.0%                                                         V-HB-TTC (No. 64)                                                                              5.0%                                                         5-BTB(F)TB-3     10.0%                                                        V2-HB-TC         10.0%                                                        3-HB-TC          5.0%                                                         5-HB-C           7.0%                                                         5-BB-C           3.0%                                                         2-BTB-1          5.0%                                                         2-BTB-O1         5.0%                                                         3-HH-4           5.0%                                                         3-HHB-1          10.0%                                                        3-HHB-3          11.0%                                                        3-H2BTB-2        3.0%                                                         3-H2BTB-3        3.0%                                                         3-HB(F)TB-2      3.0%                                                         ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =127.5° C.

η=18.7 mPa·s

Δn=0.238

Δε=5.8

V_(th) =2.58 V.

COMPOSITION EXAMPLE 14

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB2BB-TTC (No. 231)                                                                            2.0%                                                       1V2-BEB(F,F)-C     6.0%                                                       3-HB-C             18.0%                                                      2-BTB-1            10.0%                                                      5-HH-VFF           30.0%                                                      1-BHH-VFF          8.0%                                                       1-BHH-2VFF         11.0%                                                      3-H2BTB-2          5.0%                                                       3-H2BTB-3          4.0%                                                       3-H2BTB-4          4.0%                                                       3-HHB-1            2.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 15

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HPy-TTC (No. 67)                                                                              2.0%                                                        2-HB-C            5.0%                                                        3-HB-C            12.0%                                                       3-HB-O2           15.0%                                                       2-BTB-1           3.0%                                                        3-HHB-1           8.0%                                                        3-HHB-F           4.0%                                                        3-HHB-O1          5.0%                                                        3-HHB-3           12.0%                                                       3-HHEB-F          4.0%                                                        5-HHEB-F          4.0%                                                        2-HHB(F)-F        7.0%                                                        3-HHB(F)-F        7.0%                                                        5-HHB(F)-F        7.0%                                                        3-HHB(F,F)-F      5.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 16

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB-TTC (No. 62)                                                                              5.0%                                                         V-HB-TTC (No. 64)                                                                              5.0%                                                         2-HHB(F)-F       17.0%                                                        3-HHB(F)-F       17.0%                                                        5-HHB(F)-F       16.0%                                                        2-H2HB(F)-F      10.0%                                                        3-H2HB(F)-F      5.0%                                                         2-HBB(F)-F       6.0%                                                         3-HBB(F)-F       6.0%                                                         5-HBB(F)-F       13.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =108.1° C.

η=26.6 mPa·s

Δn=0.127

Δε=5.9

V_(th) =1.87 V.

Further, 0.3 part by weight of the optically active compound expressedby the formula (Op-8) was added to 100 parts by weight of the primaryliquid crystal composition described above to obtain a secondary liquidcrystal composition, and a characteristic of the secondary compositionwas determined to be as follows:

P=77.4 μm.

COMPOSITION EXAMPLE 17

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        5-HH-VTC (No. 34)  3.0%                                                       V-HB-VTC (No. 39)  3.0%                                                       7-HB(F)-F          5.0%                                                       5-H2B(F)-F         5.0%                                                       3-HB-O2            10.0%                                                      3-HH-4             2.0%                                                       3-HH[5D,6D,7D]-4   3.0%                                                       2-HHB(F)-F         10.0%                                                      3-HHB(F)-F         10.0%                                                      5-HH[5D,6D,7D]B(F)-F                                                                             10.0%                                                      3-H2HB(F)-F        5.0%                                                       2-HBB(F)-F         3.0%                                                       3-HBB(F)-F         3.0%                                                       2-H2BB(F)-F        5.0%                                                       3-H2BB(F)-F        6.0%                                                       3-HHB-1            8.0%                                                       3-HHB-O1           5.0%                                                       3-HHB-3            4.0%                                                       ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =95.4° C.

η=17.7 mPa·s

Δn=0.100

Δε=3.4

V_(th) =2.52 V.

COMPOSITION EXAMPLE 18

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB-TTC (No. 62)                                                                              8.0%                                                         3-HH-TTC (No. 58)                                                                              8.0%                                                         7-HB(F,F)-F      3.0%                                                         3-HB-O2          7.0%                                                         2-HHB(F)-F       10.0%                                                        3-HHB(F)-F       10.0%                                                        5-HHB(F)-F       10.0%                                                        2-HBB(F)-F       9.0%                                                         3-HBB(F)-F       9.0%                                                         2-HBB-F          4.0%                                                         3-HBB-F          4.0%                                                         5-HBB-F          3.0%                                                         3-HBB(F,F)-F     5.0%                                                         5-HBB(F,F)-F     10.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =103.0° C.

η=22.8 mPa·s

Δn=0.151

Δε=6.5

V_(th) =1.56 V.

COMPOSITION EXAMPLE 19

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HHH-VTC (No. 84)                                                                              2.0%                                                        7-HB(F,F)-F       3.0%                                                        3-H2HB(F,F)-F     10.0%                                                       4-H2HB(F,F)-F     10.0%                                                       5-H2HB(F,F)-F     10.0%                                                       3-HHB(F,F)-F      5.0%                                                        4-HHB(F,F)-F      5.0%                                                        3-HH2B(F,F)-F     15.0%                                                       5-HH2B(F,F)-F     10.0%                                                       3-HBB(F,F)-F      12.0%                                                       5-HBB(F,F)-F      12.0%                                                       3-HBCF2OB(F,F)-F  6.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 20

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        C-BHH-VTC (No. 89)                                                                              2.0%                                                        7-HB(F,F)-F       5.0%                                                        3-H2HB(F,F)-F     12.0%                                                       4-H2HB(F,F)-F     10.0%                                                       3-HHB(F,F)-F      10.0%                                                       4-HHB(F,F)-F      5.0%                                                        3-HBB(F,F)-F      10.0%                                                       3-HHEB(F,F)-F     10.0%                                                       4-HHEB(F,F)-F     3.0%                                                        5-HHEB(F,F)-F     3.0%                                                        2-HBEB(F,F)-F     3.0%                                                        3-HBEB(F,F)-F     3.0%                                                        5-HBEB(F,F)-F     3.0%                                                        3-HGB(F,F)-F      15.0%                                                       3-HHBB(F,F)-F     6.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 21

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        F-BHH-VTC (No. 90)                                                                              2.0%                                                        3-HB-CL           10.0%                                                       5-HB-CL           4.0%                                                        7-HB-CL           4.0%                                                        1O1-HH-5          5.0%                                                        2-HBB(F)-F        8.0%                                                        3-HBB(F)-F        8.0%                                                        5-HBB(F)-F        12.0%                                                       4-HHB-CL          8.0%                                                        5-HHB-CL          8.0%                                                        3-H2HB(F)-CL      4.0%                                                        3-HBB(F,F)-F      10.0%                                                       5-H2BB(F,F)-F     9.0%                                                        3-HB(F)VB-2       4.0%                                                        3-HB(F)VB-3       4.0%                                                        ______________________________________                                    

COMPOSITION EXAMPLE 22

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB2B-VTC (No. 121)                                                                             3.0%                                                       3-HHB(F,F)-F       9.0%                                                       3-H2HB(F,F)-F      8.0%                                                       4-H2HB(F,F)-F      8.0%                                                       5-H2HB(F,F)-F      8.0%                                                       3-HBB(F,F)-F       18.0%                                                      5-HBB(F,F)-F       20.0%                                                      3-H2BB(F,F)-F      10.0%                                                      5-HHBB(F,F)-F      3.0%                                                       5-HHEBB-F          2.0%                                                       3-HH2BB(F,F)-F     3.0%                                                       1O1-HBBH-4         4.0%                                                       1O1-HBBH-5         4.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 23

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HEHB-TTC (No. 156)                                                                             2.0%                                                       5-HB-F             12.0%                                                      6-HB-F             9.0%                                                       7-HB-F             7.0%                                                       2-HHB-OCF3         7.0%                                                       3-HHB-OCF3         7.0%                                                       4-HHB-OCF3         5.0%                                                       5-HHB-OCF3         5.0%                                                       3-HH2B-OCF3        4.0%                                                       5-HH2B-OCF3        4.0%                                                       3-HHB(F,F)-OCF3    5.0%                                                       3-HBB(F)-F         10.0%                                                      5-HBB(F)-F         10.0%                                                      3-HH2B(F)-F        3.0%                                                       3-HB(F)BH-3        3.0%                                                       5-HBBH-3           3.0%                                                       3-HHB(F,F)-OCF2H   4.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 24

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HVHB-TTC (No. 151)                                                                             2.0%                                                       5-H4HB(F,F)-F      7.0%                                                       5-H4HB-OCF3        15.0%                                                      3-H4HB(F,F)-CF3    8.0%                                                       5-H4HB(F,F)-CF3    10.0%                                                      3-HB-CL            6.0%                                                       5-HB-CL            4.0%                                                       2-H2BB(F)-F        5.0%                                                       3-H2BB(F)-F        8.0%                                                       5-HVHB(F,F)-F      5.0%                                                       3-HHB-OCF3         5.0%                                                       3-H2HB-OCF3        5.0%                                                       V-HHB(F)-F         5.0%                                                       3-HHB(F)-F         5.0%                                                       5-HHEB-OCF3        2.0%                                                       3-HBEB(F,F)-F      5.0%                                                       5-HH-V2F           3.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 25

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HBTB-TTC (No. 174)                                                                             2.0%                                                       2-HHB(F)-F         2.0%                                                       3-HHB(F)-F         2.0%                                                       5-HHB(F)-F         2.0%                                                       2-HBB(F)-F         6.0%                                                       3-HBB(F)-F         6.0%                                                       5-HBB(F)-F         10.0%                                                      2-H2BB(F)-F        9.0%                                                       3-H2BB(F)-F        9.0%                                                       3-HBB(F,F)-F       23.0%                                                      5-HBB(F,F)-F       19.0%                                                      1O1-HBBH-4         5.0%                                                       1O1-HBBH-5         5.0%                                                       ______________________________________                                    

Further, 0.25 part by weight of the optically active compound expressedby the formula (Op-5) was added to 100 parts by weight of this primaryliquid crystal composition described above to obtain a secondary liquidcrystal composition, and a characteristic of the secondary compositionwas determined to be as follows:

P=77.4 μm.

COMPOSITION EXAMPLE 26

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-GHB-TTC (No. 142)                                                                              2.0%                                                       5-HB-CL            12.0%                                                      3-HH-4             7.0%                                                       3-HB-O2            20.0%                                                      3-H2HB(F,F)-F      8.0%                                                       3-HHB(F,F)-F       6.0%                                                       3-HBB(F,F)-F       6.0%                                                       2-HHB(F)-F         5.0%                                                       3-HHB(F)-F         5.0%                                                       5-HHB(F)-F         5.0%                                                       2-H2HB(F)-F        2.0%                                                       3-H2HB(F)-F        1.0%                                                       5-H2HB(F)-F        2.0%                                                       3-HHBB(F,F)-F      4.0%                                                       3-HBCF2OB-OCF3     4.0%                                                       5-HBCF2OB(F,F)-CF3 4.0%                                                       3-HHB-1            3.0%                                                       3-HHB-O1           4.0%                                                       ______________________________________                                    

COMPOSITION EXAMPLE 27

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                             15.0%                                                       3-HB-C            20.0%                                                       5-HB-C            31.0%                                                       7-HB-C            21.0%                                                       5-HBB-C           13.0%                                                       ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =84.4° C.

T_(MP) <-20° C.

η=30.5 mPa·s

Δn=0.1610

Δε=11.3

V_(th) =1.70 V.

COMPOSITION EXAMPLE 28

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 246)                                                                              15.0%                                                       3-HB-C            20.0%                                                       5-HB-C            31.0%                                                       7-HB-C            21.0%                                                       5-HBB-C           13.0%                                                       ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =83.0° C.

T_(MP) <-20° C.

η=30.4 mPa·s

Δn=0.162

Δε=11.8

V_(th) =1.57 V.

COMPOSITION EXAMPLE 29

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                             11.0%                                                       1V2-BEB(F,F)-C    5.0%                                                        3-HB-C            20.0%                                                       1-BTB-3           5.0%                                                        2-BTB-1           10.0%                                                       3-HH-4            11.0%                                                       3-HHB-1           11.0%                                                       3-HHB-3           9.0%                                                        3-H2BTB-2         4.0%                                                        3-H2BTB-3         4.0%                                                        3-H2BTB-4         4.0%                                                        3-HB(F)TB-2       6.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =95.3° C.

T_(MP) <-30° C.

η=17.2 mPa·s

Δn=0.174

Δε=7.8

V_(th) =1.91 V.

Further, 0.8 part by weight of the optically active compound expressedby the formula (Op-4) was added to 100 parts by weight of the primaryliquid crystal composition described above to obtain a secondary liquidcrystal composition, and a characteristic of the secondary compositionwas determined to be as follows:

P=11.5 μm.

COMPOSITION EXAMPLE 30

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 246)                                                                              11.0%                                                       V2-HB-C           12.0%                                                       1V2-HB-C          12.0%                                                       3-HB-C            10.0%                                                       3-H[1D,2D,3D]-C   9.0%                                                        3-HB(F)-C         5.0%                                                        2-BTB-1           2.0%                                                        3-HH-4            8.0%                                                        3-HH-VFF          6.0%                                                        2-H[1D,2D,3D]HB-C 3.0%                                                        3-HHB-C           6.0%                                                        3-HB(F)TB-2       8.0%                                                        3-H2BTB-2         5.0%                                                        3-H2BTB-3         3.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =92.6° C.

T_(MP) <-30° C.

η=19.9 mPa·s

Δn=0.166

Δε=9.6

V_(th) =1.80 V.

COMPOSITION EXAMPLE 31

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        V-HB-TVC (No. 252)                                                                              8.0%                                                        2O1-BEB(F)-C      5.0%                                                        3O1-BEB(F)-C      15.0%                                                       4O1-BEB(F)-C      13.0%                                                       5O1-BEB(F)-C      13.0%                                                       2-HHB(F)-C        15.0%                                                       3-HHB(F)-C        15.0%                                                       3-HB(F)TB-2       4.0%                                                        3-HHB-1           8.0%                                                        3-HHB-O1          4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =89.2° C.

T_(MP) <-30° C.

η=89.1 mPa·s

Δn=0.157

Δε=32.3

V_(th) =0.82 V.

COMPOSITION EXAMPLE 32

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 246)                                                                              10.0%                                                       5-H2B-TVC (No. 250)                                                                             10.0%                                                       5-PyB-F           4.0%                                                        3-PyB(F)-F        4.0%                                                        2-BB-C            5.0%                                                        4-BB-C            4.0%                                                        5-BB-C            5.0%                                                        2-PyB-2           2.0%                                                        3-PyB-2           2.0%                                                        4-PyB-2           2.0%                                                        6-PyB-O5          3.0%                                                        6-PyB-O6          3.0%                                                        6-PyB-O7          3.0%                                                        6-PyB-O8          3.0%                                                        3-PyBB-F          6.0%                                                        4-PyBB-F          6.0%                                                        5-PyBB-F          6.0%                                                        3-HHB-1           6.0%                                                        3-HHB-3           8.0%                                                        2-H2BTB-2         4.0%                                                        2-H2BTB-3         4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =87.4° C.

T_(MP) <-20° C.

η=40.6 mPa·s

Δn=0.213

Δε=9.5

V_(th) =1.86 V.

COMPOSITION EXAMPLE 33

Liquid crystal composition comprising the following compounds amountshown below was prepared:

    ______________________________________                                        3-HB-TVC (No. 247)                                                                              10.0%                                                       3-DB-C            10.0%                                                       4-DB-C            10.0%                                                       2-BEB-C           12.0%                                                       3-BEB-C           4.0%                                                        3-PyB(F)-F        6.0%                                                        3-HEB-O4          8.0%                                                        4-HEB-O2          6.0%                                                        3-HEB-O2          5.0%                                                        5-HEB-5           5.0%                                                        4-HEB-5           5.0%                                                        1O-BEB-2          4.0%                                                        3-HHB-1           6.0%                                                        3-HHEBB-C         3.0%                                                        3-HBEBB-C         3.0%                                                        5-HBEBB-C         3.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =77.9° C.

η=42.6 mPa·s

Δn=0.144

Δε=13.0

V_(th) =1.20 V.

COMPOSITION EXAMPLE 34

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        V2-HB-TVC (No. 253)                                                                              6.0%                                                       3-HB-C             18.0%                                                      7-HB-C             3.0%                                                       1O1-HB-C           10.0%                                                      3-HB(F)-C          10.0%                                                      2-PyB-2            2.0%                                                       3-PyB-2            2.0%                                                       4-PyB-2            2.0%                                                       1O1-HH-3           7.0%                                                       2-BTB-O1           7.0%                                                       3-HHB-1            7.0%                                                       3-HHB-F            4.0%                                                       3-HHB-O1           4.0%                                                       3-HHB-3            8.0%                                                       3-H2BTB-2          3.0%                                                       2-PyBH-3           4.0%                                                       3-PyBB-2           3.0%                                                       ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =78.2° C.

η=18.8 mPa·s

Δn=0.144

Δε=8.9

V_(th) =1.68 V.

COMPOSITION EXAMPLE 35

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        V-HB-TVC (No. 252)                                                                              7.0%                                                        5-BEB(F)-C        5.0%                                                        V-HB-C            11.0%                                                       5-PyB-C           6.0%                                                        4-BB-3            11.0%                                                       3-HH-2V           10.0%                                                       5-HH-V            5.0%                                                        V2V-HH-3          6.0%                                                        V-HHB-1           7.0%                                                        V2-HHB-1          15.0%                                                       3-HHB-1           9.0%                                                        1V2-HBB-2         3.0%                                                        3-HHEBH-3         5.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =92.3° C.

η=17.0 mPa·s

Δn=0.123

Δε=5.8

V_(th) =2.28 V.

COMPOSITION EXAMPLE 36

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                              10.0%                                                      2-HB-TVC (No. 246) 10.0%                                                      V-HB-TVC (No. 252) 5.0%                                                       V2-HB-TVC (No. 253)                                                                              5.0%                                                       2O1-BEB(F)-C       5.0%                                                       3O1-BEB(F)-C       12.0%                                                      5O1-BEB(F)-C       4.0%                                                       1V2-BEB(F,F)-C     16.0%                                                      3-HB-O2            6.0%                                                       3-HH-4             3.0%                                                       3-HHB-F            3.0%                                                       3-HHB-1            3.0%                                                       3-HHB-O1           4.0%                                                       3-HBEB-F           4.0%                                                       3-HHEB-F           3.0%                                                       3-H2BTB-2          4.0%                                                       3-HB(F)TB-2        3.0%                                                       ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =93.3° C.

η=49.1 mPa·s

Δn=0.189

Δε=32.2

V_(th) =0.88 V.

COMPOSITION EXAMPLE 37

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 246)                                                                              6.0%                                                        V-HB-TVC (No. 252)                                                                              7.0%                                                        2-BEB-C           10.0%                                                       5-BB-C            12.0%                                                       7-BB-C            7.0%                                                        1-BTB-3           7.0%                                                        2-BTB-1           10.0%                                                       1O-BEB-2          10.0%                                                       1O-BEB-5          12.0%                                                       2-HHB-1           4.0%                                                        3-HHB-F           4.0%                                                        3-HHB-1           7.0%                                                        3-HHB-O1          4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =65.8° C.

η=23.6 mPa·s

Δn=0.185

Δε=8.5

V_(th) =1.61 V.

COMPOSITION EXAMPLE 38

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB-TVC (No. 247)                                                                              5.0%                                                        5-BTB(F)TB-3      10.0%                                                       V2-HB-TC          10.0%                                                       3-HB-TC           10.0%                                                       3-HB-C            10.0%                                                       5-HB-C            7.0%                                                        5-BB-C            3.0%                                                        2-BTB-1           10.0%                                                       2-BTB-O1          5.0%                                                        3-HH-4            3.0%                                                        3-HHB-1           10.0%                                                       3-HHB-3           11.0%                                                       3-H2BTB-2         3.0%                                                        3-HB(F)TB-2       3.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =101.5° C.

η=15.7 mPa·s

Δn=0.213

Δε=7.4

V_(th) =2.00 V.

COMPOSITION EXAMPLE 39

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 246)                                                                              10.0%                                                       1V2-BEB(F,F)-C    6.0%                                                        3-HB-C            18.0%                                                       2-BTB-1           8.0%                                                        5-HH-VFF          30.0%                                                       1-BHH-VFF         8.0%                                                        1-BHH-2VFF        11.0%                                                       3-H2BTB-2         5.0%                                                        3-HHB-1           4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =81.3° C.

η=14.9 mPa·s

Δn=0.135

Δε=8.0

V_(th) =1.89 V.

COMPOSITION EXAMPLE 40

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 224)                                                                              8.0%                                                        3-HB-TVC (No. 247)                                                                              5.0%                                                        2-HHB(F)-F        17.0%                                                       3-HHB(F)-F        17.0%                                                       5-HHB(F)-F        16.0%                                                       2-H2HB(F)-F       10.0%                                                       3-H2HB(F)-F       5.0%                                                        5-H2HB(F)-F       10.0%                                                       2-HBB(F)-F        6.0%                                                        3-HBB(F)-F        6.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =105.2° C.

η=28.5 mPa·s

Δn=0.116

Δε=6.1

V_(th) =2.05 V.

Further, 0.3 part by weight of the optically active compound expressedby the formula (Op-8) was added to 100 parts by weight of the primaryliquid crystal composition described above to obtain a secondary liquidcrystal composition, and a characteristic of the secondary compositionwas determined to be as follows:

P=82 μm

COMPOSITION EXAMPLE 41

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                              6.0%                                                       7-HB(F)-F          5.0%                                                       5-H2B(F)-F         5.0%                                                       3-HB-O2            10.0%                                                      3-HH-4             2.0%                                                       3-HH[5D,6D,7D]-4   3.0%                                                       2-HHB(F)-F         10.0%                                                      3-HHB(F)-F         10.0%                                                      5-HH[5D,6D,7D]B(F)-F                                                                             10.0%                                                      3-H2HB(F)-F        5.0%                                                       2-HBB(F)-F         3.0%                                                       3-HBB(F)-F         3.0%                                                       2-H2BB(F)-F        5.0%                                                       3-H2BB(F)-F        6.0%                                                       3-HHB-1            8.0%                                                       3-HHB-O1           5.0%                                                       3-HHB-3            4.0%                                                       ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =91.7° C.

η=19.4 mPa·s

Δn=0.109

Δε=3.8

V_(th) =2.59 V.

COMPOSITION EXAMPLE 42

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-HB-TVC (No. 247)                                                                              10.0%                                                       7-HB(F,F)-F       5.0%                                                        3-H2HB(F,F)-F     12.0%                                                       4-H2HB(F,F)-F     10.0%                                                       4-HHB(F,F)-F      5.0%                                                        3-HBB(F,F)-F      10.0%                                                       3-HHEB(F,F)-F     10.0%                                                       4-HHEB(F,F)-F     3.0%                                                        5-HHEB(F,F)-F     3.0%                                                        2-HBEB(F,F)-F     3.0%                                                        3-HBEB(F,F)-F     5.0%                                                        5-HBEB(F,F)-F     3.0%                                                        3-HGB(F,F)-F      15.0%                                                       3-HHBB(F,F)-F     6.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =81.2° C.

η=36.6 mPa·s

Δn=0.107

Δε=13.5

V_(th) =1.32 V.

COMPOSITION EXAMPLE 43

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                             7.0%                                                        2-HB-TVC (No. 246)                                                                              7.0%                                                        3-HB-CL           10.0%                                                       5-HB-CL           4.0%                                                        7-HB-CL           4.0%                                                        1O1-HH-5          5.0%                                                        2-HBB(F)-F        8.0%                                                        3-HBB(F)-F        8.0%                                                        4-HHB-CL          8.0%                                                        5-HHB-CL          8.0%                                                        3-H2HB(F)-CL      4.0%                                                        3-HBB(F,F)-F      10.0%                                                       5-H2BB(F,F)-F     9.0%                                                        3-HB(F)VB-2       4.0%                                                        3-HB(F)VB-3       4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =98.6° C.

η=24.5 mPa·s

Δn=0.153

Δε=6.0

V_(th) =2.06 V.

COMPOSITION EXAMPLE 44

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                             5.0%                                                        2-HB-FVC (No. 246)                                                                              5.0%                                                        5-HB-F            12.0%                                                       6-HB-F            9.0%                                                        7-HB-F            7.0%                                                        2-HHB-OCF3        7.0%                                                        3-HHB-OCF3        7.0%                                                        4-HHB-OCF3        7.0%                                                        5-HHB-OCF3        5.0%                                                        3-HH2B-OCF3       4.0%                                                        5-HH2B-OCF3       4.0%                                                        3-HHB(F,F)-OCF3   5.0%                                                        3-HBB(F)-F        10.0%                                                       3-HH2B(F)-F       3.0%                                                        3-HB(F)BH-3       3.0%                                                        5-HBBH-3          3.0%                                                        3-HHB(F,F)-OCF2H  4.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =91. 0° C.

η=17.4 mPa·s

Δn=0.109

Δε=5.5

V_(th) =2.20 V.

COMPOSITION EXAMPLE 45

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        3-H2B-TVC (No. 249)                                                                             5.0%                                                        3-HB-TVC (No. 247)                                                                              5.0%                                                        5-H4HB(F,F)-F     7.0%                                                        5-H4HB-OCF3       15.0%                                                       3-H4HB(F,F)-CF3   8.0%                                                        5-H4HB(F,F)-CF3   10.0%                                                       3-HB-CL           6.0%                                                        5-HB-CL           4.0%                                                        2-H2BB(F)-F       5.0%                                                        5-HVHB(F,F)-F     5.0%                                                        3-HHB-OCF3        5.0%                                                        3-H2HB-OCF3       5.0%                                                        V-HHB(F)-F        5.0%                                                        3-HHB(F)-F        5.0%                                                        5-HHEB-OCF3       2.0%                                                        3-HBEB(F,F)-F     5.0%                                                        5-HH-V2F          3.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =76.4° C.

η=27.3 mPa·s

Δn=0.112

Δε=9.2

V_(th) =1.58 V.

COMPOSITION EXAMPLE 46

Liquid crystal composition comprising the following compounds in theamount shown below was prepared:

    ______________________________________                                        2-HB-TVC (No. 246)                                                                              4.0%                                                        V-HB-TVC (No. 252)                                                                              3.0%                                                        5-H2B-TVC (No. 250)                                                                             3.0%                                                        2-HHB(F)-F        2.0%                                                        3-HHB(F)-F        2.0%                                                        5-HHB(F)-F        2.0%                                                        2-HBB(F)-F        6.0%                                                        3-HBB(F)-F        6.0%                                                        2-H2BB(F)-F       9.0%                                                        3-H2BB(F)-F       9.0%                                                        3-HBB(F,F)-F      25.0%                                                       5-HBB(F,F)-F      19.0%                                                       1O1-HBBH-4        5.0%                                                        1O1-HBBH-5        5.0%                                                        ______________________________________                                    

Characteristics of this composition were determined to be as follows:

T_(NI) =101.1° C.

η=37.9 mPa·s

Δn=0.153

Δε=8.2

V_(th) =1.72 V.

Compounds of the present invention expressed by the general formula (1)can be produced by known general methods of organic synthesis.

Production of the compounds expressed by the general formula (1) whereinG represents the group expressed by the formula (3) or (4) describedabove, and ring A₄ is 1,4-cyclohexylene or 1,3-dioxane-2,5-diyl.

A halide expressed by the general formula (18) can readily be producedby synthesizing aldehyde (17) according to a method described inShin-Jikken Kagaku Kouza, vol. 14, p 633 (1977), and converting it bythe method (a) or (b) described below.

(a) A method described in Shin-Jikken Kagaku Kouza, vol. 14, p 633(1977) and Organic Reactions, vol. 14, p 270 (1965) in the case where G₁is 1,2-ethenylene,

(b) A method described in Tetrahedron Lett., vol. 37, 2763 (1996) andPreparative Acetylenic Chemistry, second edition, ELSEVIER (1988) in thecase where G₁ is 1,2-ethynylene.

A compound expressed by the general formula (19) can readily be obtainedby subjecting the halide (18) thus formed to a coupling reaction with2-methyl-3-butyne-2-ol in a suitable solvent in the presence of acatalyst of a transition metal complex and a promoter added whennecessary (reference is mate to the literature mentioned in (b) above).

As examples of the complex catalyst described above, zero valent ordivalent palladium complexes such as dichlorobistriphenylphosphinepalladium, tetrakistriphenylphosphine palladium, palladium acetate, andKharasch complex can be mentioned. While the amount of the complexcatalyst to be used is not constant since it depends on the reactivityof substrates, the range of 0.1 to 20% by mol to halide (18) isgenerally suitable, and the range of 0.5 to 5% by mol is preferablesince conversion time is short and side reactions hardly occur besides.

As example of the promoter, copper salts such as copper iodide andcopper bromide can be mentioned, and the use of these salts ispreferable for increasing the yield of compound (19).

As examples of most suitable solvent to be used, while diethylamine cangenerally be mentioned, a polar solvent such as triethylamine, pyridine,pyrrolidine, morpholine, and dimethyl formamide, and a mixed solvent ofone of these solvents with another solvent can be used.

While reaction temperature may be in the range from -40° C. to theboiling point of a solvent to be used, it is preferable to use thetemperature particularly between 0° C. and the boiling point of thesolvent since an excellent activity of the complex catalyst can beretained and the conversion can be maintained at a high level. In thisconnection, since the active site of the complex catalyst is unstableagainst air and moisture in the reaction described above, the reactionis preferably carried out in an inert gas as a countermeasure.

The compound (19) obtained by the method described above is treatedaccording to a method described in the Preparative Acetylenic Chemistry,second edition, ELSEVIER (1988), and led to the compound of the presentinvention expressed by the general formula (1).

That is, the compound (19) obtained by the method described above istreated with a base such as potassium hydroxide in a suitable solvent toreadily deprotect, thereby being converted into a compound expressed bythe general formula (20). A halide expressed by the general formula (21)can be synthesized by reacting the compound (20) with a base such asn-butyl lithium (n-BuLi) in an aprotic solvent such as tetrahydrofuran(THF), and then reacting with a halogen such as iodine and bromine.Compounds of the present invention included in the general formula (1)can be obtained by reacting the halide (21) with copper cyanide in asolvent such as THF and N,N-dimethyl formamide (DMF) in which a catalystsuch as lithium bromide is added when required.

Subsequent to the reactions described above, the reaction solution issubjected to an after-treatment according to a conventional method, andfurther subjected to purifying operations such as distillation,recrystallization, and column chromatography to isolate the compound(1). ##STR25## wherein R, A₁, A₂, A₃, A₄, B₁, B₂, B₃, G, m, n, and phave the same meaning as described above, G represents the groupexpressed the formula (3) or (4), and X represents a halogen atom.

Production of the compounds expressed by the general formula (1) whereinG represents the group expressed by the formula (3) or (4), and A₄represents 1,4-phenylene in which hydrogen atom on the ring may bereplaced by fluorine atom, or pyrimidine-2,5-diyl group:

A compound corresponding to the compound (20) described above canreadily be obtained by performing a coupling reaction with halide (18)in the same manner as described above with the exception that(trimethylsilyl)acetylene is used instead of 2-methyl-3-butyne-2-ol toobtain a compound expressed by the general formula (22), and thendeprotecting it with potassium fluoride in a solvent such as DMF. Thiscompound can be converted into a compound which is an an example thoseof the present invention expressed by the general formula (1) by thesame manner as described above. ##STR26## wherein R, A₁, A₂, A₃, A₄, B₁,B₂, B₃, G, m, n, and p have the same meaning as described above, and Grepresents the group expressed the formula (3) or (4).

Production of the compounds expressed by the general formula (1) whereinG represents the group expressed by the formula (2) described above:

A compound of the present invention expressed by the general formula (1)can be obtained by reacting a known ethynylene derivative expressed bythe general formula (23) with 1,2-dihalogenoethylene in a dipolaraprotic solvent or basic solvent in the presence of a transition metalcatalyst (for example, dichlorobistriphenylphosphine palladium) toconvert into a vinyl halide derivative expressed by the general formula(24), and then reacting it with a metal cyanide such as copper cyanidein a suitable polar solvent such as N-methylpyrrolidone (NMP). ##STR27##wherein R, A₁, A₂, A₃, A₄, B₁, B₂, B₃, G, m, n, and p have the samemeaning as described above.

BEST MODE FOR CARRYING OUT THE INVENTION

Now the present invention will be described in more detail withreference to Examples. However, it should be understood that the scopeof the present invention is by no means restricted by such specificExamples.

In each of the Examples, C indicate crystal, N: nematic phase, S:smectic phase, and I: isotropic liquid phase, and the unit of all phasetransition temperatures is ° C.

EXAMPLE 1

Preparation oftrans-4-(trans-4-pentylcyclohexyl)-1-(4-cyano-1-E-butene-3-yne-1-yl)cyclohexane(Compound expressed by the general formula (1) wherein R is pentylgroup, m=n=0, p=1, both A₃ and A₄ are 1,4-cyclohexylene group, B₃ is acovalent bond, and G is the group expressed by the formula (3), CompoundNo. 34)

To a mixture oftrans-4-(trans-4-pentylcyclohexyl)-1-(2-E-bromovinyl)cyclohexane (66mmol), 2-methyl-3-butyne-2-ol (132 mmol), dichlorobistriphenylphosphinepalladium (2.0 mmol), and copper iodide (7.4 mmol) was added by dropspyrrolidine, and stirred at room temperature under argon gas atmosphereovernight.

Aqueous ammonium chloride solution was added to the reaction solution,and extracted with toluene twice. The organic layer thus obtained waswashed with an aqueous sodium chloride solution and dried over anhydrousmagnesium sulfate. After filtration, the solvent was distilled off undera reduced pressure. The residue was purified by column chromatography(silica gel/toluene:ethyl acetate=10:1) to obtain colorless crystals oftrans-4-(trans-4-pentylcyclohexyl)-1-(5-hydroxy-5,5-dimethyl-1-E-pentene-3-yne-1-yl)cyclohexane.(Yield 92%)

This compound (58 mmol) and powdered potassium hydroxide (0.36 mmol)were refluxed in toluene for 2 hours. After it was cooled, 3Nhydrochloric acid was added thereto until pH became 1, and then theorganic layer was isolated. The water layer was further extracted withtoluene, combined with the organic layer mentioned above, and thenwashed with a saturated aqueous sodium bicarbonate solution. After thelayer was dried over anhydrous magnesium sulfate, it was subjected tofiltration, and the solvent was distilled off under a reduced pressure.The residue was purified by column chromatography (silica gel/heptane)and recrystallization (ethanol) to obtain colorless crystals oftrans-4-(trans-4-pentylcyclohexyl)-1-(1-E-butene-3-yne-lyl)cyclohexane.(Yield 54%).

To a solution of this compound (34 mmol) in THF was added a solution ofn-butyl lithium (38 mmol) in THF at -60° C., and then stirred for 1hour. Subsequently, a solution of iodine (38 mmol) in THF was addedthereto at a temperature lower than -30° C., and then allowed to standuntil the temperature of the reaction mixture became 0° C. After anaqueous ammonium chloride solution was added to the reaction solution,and extracted with toluene twice, the organic layer was washed with anaqueous sodium thiosulfate solution and with an aqueous sodium chloridesolution. The organic layer was dried over anhydrous magnesium sulfate.After the layer was subjected to filtration, the solvent was distilledoff under a reduced pressure to obtaintrans-4-(trans-4-pentylcyclohexyl)1-(4-iodo-1-E-butene-3-yne-lyl)cyclohexane. (Yield 92%). This unpurifiedcompound (31 mmol), copper cyanide (39 mmol), and lithium bromide (11mmol) were refluxed in THF for 6 hours. After it was cooled, thereaction mixture was poured into 10% aqueous iron (II) chloride solutionand extracted with toluene twice. After the organic layer was washedwith an aqueous sodium chloride solution, dried over anhydrous magnesiumsulfate, and then subjected to filtration, the solvent was distilled offunder a reduced pressure. The residue was purified by columnchromatography (silica gel/heptane) and recrystallization (heptane) toobtain colorless crystals of the objectivetrans-4-(trans-4-pentylcyclohexyl)-1-(4-cyano-1-E-butene-3-yne-1-yl)cyclohexane.

(Yield 57%); MS; m/e=311 (M+); Phase transition points C. 42.8 N. 212(dec. >170).I; Data of each spectrum of this compound and that of eachstage well supported their structure.

EXAMPLE 2

Preparation of4-(trans-4-propylcyclohexyl)-1-(4-cyano-1,3-butadiyne-1-yl)benzene(Compound expressed by the general formula (1) wherein R is propylgroup, m=n=0, p=1, A₃ is 1,4-cyclohexylene group, A₄ is 1,4-phenylenegroup, B₃ is a covalent bond, G is the group expressed by the formula(4), Compound No. 62)

To a mixture of dichlorobistriphenylphosphine palladium (4.2 mmol) andcopper iodide (0.64 mmol) was added diethylamine, and stirred at roomtemperature under argon gas atmosphere for 30 minutes. Then,4-(trans-4-propylcyclohexyl)-1-(2-iodoethynyl)benzene (0.12 mol) wasadded thereto, and further stirred at room temperature for 15 minutes.To this reaction mixture was added (trimethylsilyl)acetylene (0.14 mol),and stirred at room temperature overnight. After completion of thereaction, water was added thereto and extracted with toluene twice. Theorganic layer thus obtained was washed with water, and then dried overanhydrous magnesium sulfate. After it was subjected to filtration, thesolvent was distilled off under a reduced pressure. The residue waspurified by column chromatography (silica gel/heptane) andrecrystallization (ethanol) to obtain colorless crystals of4-(trans-4-propylcyclohexyl)-1-(4-trimethylsilyl-1,3-butadiyne-1-yl)benzene.(Yield 24%).

To this compound (26 mmol) was added potassium fluoride (59 mol), andthen stirred in DMF at room temperature for 4 hours. After it wascooled, water was added thereto, and extracted with heptane twice, theorganic layer thus obtained was dried over anhydrous magnesium sulfate.After it was subjected to filtration, the solvent was distilled offunder a reduced pressure to obtain4-(trans-4-propylcyclohexyl)-1-(1,3-butadiyne-1-yl)benzene. (Yield 67%).

To a solution of this unpurified compound (16 mmol) in THF was added asolution of n-butyl lithium (18 mmol) in THF at -60° C., and furtherstirred for 1 hour. Subsequently, a solution of iodine (18 mmol) in THFwas added thereto at a temperature lower than -30° C., and the reactionmixture was allowed to stand until its temperature became 0° C. After anaqueous ammonium chloride solution was added to the reaction solutionand extracted with toluene twice, the organic layer thus obtained waswashed with an aqueous sodium thiosulfate solution and with an aqueoussodium chloride solution, and then dried over anhydrous magnesiumsulfate. After it was subjected to filtration, the solvent was distilledoff under a reduced pressure to obtain4-(trans-4-propylcyclohexyl)-1-(4-iodo-1,3-butadiyne-1-yl)benzene.(Yield 100%).

This unpurified compound (16 mmol), copper cyanide (20 mmol), andlithium bromide (5.9 mmol) were refluxed in THF for 5 hours. After itwas cooled, the reaction mixture was poured into 10% aqueous iron (II)chloride solution, and the solution was extracted with toluene twice.After the organic layer thus obtained was washed with an aqueous sodiumchloride solution, it was dried over anhydrous magnesium sulfate. Afterit was subjected to filtration, the solvent was distilled off under areduced pressure. The residue was purified by column chromatography(silica gel/heptane→heptane:toluene=5:1) and recrystallization (heptane)to obtain pale yellow crystals of4-(trans-4-propylcyclohexyl)-1-(4-cyano-1,3-butadiyne-1-yl)benzene.(Yield 78%).

MS; m/e=275 (M+); Phase transition points C. 71.3.N.dec.>150; Data ofeach spectrum of this compound and that of each stage well supportedtheir structure.

EXAMPLE 3

According to the method of Example 1,trans-4-(trans-4-propylcyclohexyl)-1-(4-cyano-1,3-butadiyne-1-yl)cyclohexane(Compound No. 56) was synthesized.

EXAMPLE 4

According to the method of Example2,4-(trans-4-ethenylcyclohexyl)-1-(4-cyano-1,3-butadiyne-1-yl)benzene(Compound No. 64) was synthesized.

EXAMPLE 5

According to the method of Example 1,trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)-1-(4-cyano-1-E-butene-3-yne-1-yl)cyclohexane(Compound No. 84) was synthesized.

EXAMPLE 6

According to the method of Example 1,trans-4-(trans-4-(4-fluorophenyl)cyclohexyl)-1-(4-cyano-1-E-butene-3-yne-1-yl)cyclohexane(Compound No. 90) was synthesized.

EXAMPLE 7

According to the method of Example 2,4-(trans-4(2-E-(trans-4-propylcyclohexyl)ethenylene-1-yl)cyclohexyl)-1-(4-cyano-1,3-butadiyne-1-yl)benzene(Compound No. 151) was synthesized.

EXAMPLE 8

According to the method of Example 2,4-(trans-4-propylcyclohexyl)-4'-(4-cyano-1,3-butadiyne-1-yl)tolan(Compound No. 174) was synthesized.

EXAMPLE 9

According to the method of Example 2,4-(4-(trans-4-propylcyclohexyl)phenethyl)-4'-(4-cyano-1,3-butadiyne-1-yl)biphenyl(Compound No. 198) was synthesized.

According to Examples 1 to 9 described above, the following compounds ofNo. 1 through No. 244 can be prepared.

In the following, compounds obtained by one of Examples 1 to 9 aredescribed again.

    __________________________________________________________________________    m = n = p = 0                                                                 No.                                                                              R         A.sub.4        G                                                 __________________________________________________________________________     1 CH.sub.3                                                                                 ##STR28##                                                                                    ##STR29##                                         2 C.sub.2 H.sub.5                                                                          ##STR30##                                                                                    ##STR31##                                         3 n-C.sub.3 H.sub.7                                                                        ##STR32##                                                                                    ##STR33##                                         4 n-C.sub.5 H.sub.11                                                                       ##STR34##                                                                                    ##STR35##                                         5                                                                                ##STR36##                                                                               ##STR37##                                                                                    ##STR38##                                         6 CH.sub.3                                                                                 ##STR39##                                                                                    ##STR40##                                         7 C.sub.2 H.sub.5                                                                          ##STR41##                                                                                    ##STR42##                                         8 n-C.sub.3 H.sub.7                                                                        ##STR43##                                                                                    ##STR44##                                         9 n-C.sub.5 H.sub.11                                                                       ##STR45##                                                                                    ##STR46##                                         10                                                                               ##STR47##                                                                               ##STR48##                                                                                    ##STR49##                                         11                                                                              C.sub.2 H.sub.5 O                                                                        ##STR50##                                                                                    ##STR51##                                         12                                                                              CH.sub.3                                                                                 ##STR52##                                                                                    ##STR53##                                         13                                                                              C.sub.2 H.sub.5                                                                          ##STR54##                                                                                    ##STR55##                                         14                                                                              n-C.sub.3 H.sub.7                                                                        ##STR56##                                                                                    ##STR57##                                         15                                                                              n-C.sub.5 H.sub.11                                                                       ##STR58##                                                                                    ##STR59##                                         16                                                                               ##STR60##                                                                               ##STR61##                                                                                    ##STR62##                                         17                                                                              CH.sub.3                                                                                 ##STR63##                                                                                    ##STR64##                                         18                                                                              C.sub.2 H.sub.5                                                                          ##STR65##                                                                                    ##STR66##                                         19                                                                              n-C.sub.3 H.sub.7                                                                        ##STR67##                                                                                    ##STR68##                                         20                                                                              n-C.sub.5 H.sub.11                                                                       ##STR69##                                                                                    ##STR70##                                         21                                                                               ##STR71##                                                                               ##STR72##                                                                                    ##STR73##                                         22                                                                              C.sub.2 H.sub.5 O                                                                        ##STR74##                                                                                    ##STR75##                                         23                                                                              n-C.sub.3 H.sub.7                                                                        ##STR76##                                                                                    ##STR77##                                         24                                                                              n-C.sub.5 H.sub.11                                                                       ##STR78##                                                                                    ##STR79##                                         25                                                                              n-C.sub.3 H.sub.7                                                                        ##STR80##                                                                                    ##STR81##                                         26                                                                              n-C.sub.5 H.sub.11                                                                       ##STR82##                                                                                    ##STR83##                                         27                                                                              n-C.sub.3 H.sub.7                                                                        ##STR84##                                                                                    ##STR85##                                         28                                                                              n-C.sub.5 H.sub.11                                                                       ##STR86##                                                                                    ##STR87##                                         29                                                                              n-C.sub.3 H.sub.7                                                                        ##STR88##                                                                                    ##STR89##                                         30                                                                              n-C.sub.5 H.sub.11                                                                       ##STR90##                                                                                    ##STR91##                                        __________________________________________________________________________    m = n = 0, p = 1                                                              No.                                                                              R    A.sub.3    B.sub.3                                                                         A.sub.4    G                                             __________________________________________________________________________     31                                                                              CH.sub.3                                                                            ##STR92## --                                                                               ##STR93##                                                                                ##STR94##                                     32                                                                              C.sub.2 H.sub.5                                                                     ##STR95## --                                                                               ##STR96##                                                                                ##STR97##                                     33                                                                              n-C.sub.3 H.sub.7                                                                   ##STR98## --                                                                               ##STR99##                                                                                ##STR100##                                    34                                                                              n-C.sub.5 H.sub.11                                                                  ##STR101##                                                                              --                                                                               ##STR102##                                                                               ##STR103##                                    35                                                                              CH.sub.3                                                                            ##STR104##                                                                              --                                                                               ##STR105##                                                                               ##STR106##                                    36                                                                              C.sub.2 H.sub.5                                                                     ##STR107##                                                                              --                                                                               ##STR108##                                                                               ##STR109##                                    37                                                                              n-C.sub.3 H.sub.7                                                                   ##STR110##                                                                              --                                                                               ##STR111##                                                                               ##STR112##                                    38                                                                              n-C.sub.5 H.sub.11                                                                  ##STR113##                                                                              --                                                                               ##STR114##                                                                               ##STR115##                                    39                                                                               ##STR116##                                                                         ##STR117##                                                                              --                                                                               ##STR118##                                                                               ##STR119##                                    40                                                                              n-C.sub.3 H.sub.7                                                                   ##STR120##                                                                              --                                                                               ##STR121##                                                                               ##STR122##                                    41                                                                              n-C.sub.5 H.sub.11                                                                  ##STR123##                                                                              --                                                                               ##STR124##                                                                               ##STR125##                                    42                                                                              n-C.sub.3 H.sub.7                                                                   ##STR126##                                                                              --                                                                               ##STR127##                                                                               ##STR128##                                    43                                                                              n-C.sub.5 H.sub.11                                                                  ##STR129##                                                                              --                                                                               ##STR130##                                                                               ##STR131##                                    44                                                                              CH.sub.3                                                                            ##STR132##                                                                              --                                                                               ##STR133##                                                                               ##STR134##                                    45                                                                              n-C.sub.3 H.sub.7                                                                   ##STR135##                                                                              --                                                                               ##STR136##                                                                               ##STR137##                                    46                                                                              n-C.sub.5 H.sub.11                                                                  ##STR138##                                                                              --                                                                               ##STR139##                                                                               ##STR140##                                    47                                                                              C.sub.2 H.sub.5 O                                                                   ##STR141##                                                                              --                                                                               ##STR142##                                                                               ##STR143##                                    48                                                                              NC                                                                                  ##STR144##                                                                              --                                                                               ##STR145##                                                                               ##STR146##                                    49                                                                              F                                                                                   ##STR147##                                                                              --                                                                               ##STR148##                                                                               ##STR149##                                    50                                                                              CH.sub.3                                                                            ##STR150##                                                                              --                                                                               ##STR151##                                                                               ##STR152##                                    51                                                                              C.sub.2 H.sub.5                                                                     ##STR153##                                                                              --                                                                               ##STR154##                                                                               ##STR155##                                    52                                                                              n-C.sub.3 H.sub.7                                                                   ##STR156##                                                                              --                                                                               ##STR157##                                                                               ##STR158##                                    53                                                                              n-C.sub.5 H.sub.11                                                                  ##STR159##                                                                              --                                                                               ##STR160##                                                                               ##STR161##                                    54                                                                              n-C.sub.3 H.sub.7                                                                   ##STR162##                                                                              --                                                                               ##STR163##                                                                               ##STR164##                                    55                                                                              n-C.sub.5 H.sub.11                                                                  ##STR165##                                                                              --                                                                               ##STR166##                                                                               ##STR167##                                    56                                                                              CH.sub.3                                                                            ##STR168##                                                                              --                                                                               ##STR169##                                                                               ##STR170##                                    57                                                                              C.sub.2 H.sub.5                                                                     ##STR171##                                                                              --                                                                               ##STR172##                                                                               ##STR173##                                    58                                                                              n-C.sub.3 H.sub.7                                                                   ##STR174##                                                                              --                                                                               ##STR175##                                                                               ##STR176##                                    59                                                                              n-C.sub.5 H.sub.11                                                                  ##STR177##                                                                              --                                                                               ##STR178##                                                                               ##STR179##                                    60                                                                              CH.sub.3                                                                            ##STR180##                                                                              --                                                                               ##STR181##                                                                               ##STR182##                                    61                                                                              C.sub.2 H.sub.5                                                                     ##STR183##                                                                              --                                                                               ##STR184##                                                                               ##STR185##                                    62                                                                              n-C.sub.3 H.sub.7                                                                   ##STR186##                                                                              --                                                                               ##STR187##                                                                               ##STR188##                                    63                                                                              n-C.sub.5 H.sub.11                                                                  ##STR189##                                                                              --                                                                               ##STR190##                                                                               ##STR191##                                    64                                                                               ##STR192##                                                                         ##STR193##                                                                              --                                                                               ##STR194##                                                                               ##STR195##                                    65                                                                              n-C.sub.3 H.sub.7                                                                   ##STR196##                                                                              --                                                                               ##STR197##                                                                               ##STR198##                                    66                                                                              n-C.sub.5 H.sub.11                                                                  ##STR199##                                                                              --                                                                               ##STR200##                                                                               ##STR201##                                    67                                                                              n-C.sub.3 H.sub.7                                                                   ##STR202##                                                                              --                                                                               ##STR203##                                                                               ##STR204##                                    68                                                                              n-C.sub.5 H.sub.11                                                                  ##STR205##                                                                              --                                                                               ##STR206##                                                                               ##STR207##                                    69                                                                              CH.sub.3                                                                            ##STR208##                                                                              --                                                                               ##STR209##                                                                               ##STR210##                                    70                                                                              n-C.sub.3 H.sub.7                                                                   ##STR211##                                                                              --                                                                               ##STR212##                                                                               ##STR213##                                    71                                                                              n-C.sub.5 H.sub.11                                                                  ##STR214##                                                                              --                                                                               ##STR215##                                                                               ##STR216##                                    72                                                                              C.sub.2 H.sub.5 O                                                                   ##STR217##                                                                              --                                                                               ##STR218##                                                                               ##STR219##                                    73                                                                              NC                                                                                  ##STR220##                                                                              --                                                                               ##STR221##                                                                               ##STR222##                                    74                                                                              F                                                                                   ##STR223##                                                                              --                                                                               ##STR224##                                                                               ##STR225##                                    75                                                                              CH.sub.3                                                                            ##STR226##                                                                              --                                                                               ##STR227##                                                                               ##STR228##                                    76                                                                              CH.sub.3                                                                            ##STR229##                                                                              --                                                                               ##STR230##                                                                               ##STR231##                                    77                                                                              C.sub.2 H.sub.5                                                                     ##STR232##                                                                              --                                                                               ##STR233##                                                                               ##STR234##                                    78                                                                              n-C.sub.3 H.sub.7                                                                   ##STR235##                                                                              --                                                                               ##STR236##                                                                               ##STR237##                                    79                                                                              n-C.sub.5 H.sub.11                                                                  ##STR238##                                                                              --                                                                               ##STR239##                                                                               ##STR240##                                    80                                                                              n-C.sub.3 H.sub.7                                                                   ##STR241##                                                                              --                                                                               ##STR242##                                                                               ##STR243##                                    81                                                                              n-C.sub.5 H.sub.11                                                                  ##STR244##                                                                              --                                                                               ##STR245##                                                                               ##STR246##                                   __________________________________________________________________________    m = 0, n = p = 1                                                              No.  R      A.sub.2     B.sub.2  A.sub.3                                      __________________________________________________________________________     82  CH.sub.3                                                                              ##STR247## --                                                                                      ##STR248##                                   83  C.sub.2 H.sub.5                                                                       ##STR249## --                                                                                      ##STR250##                                   84  n-C.sub.3 H.sub.7                                                                     ##STR251## --                                                                                      ##STR252##                                   85  n-C.sub.5 H.sub.11                                                                    ##STR253## --                                                                                      ##STR254##                                   86  CH.sub.3                                                                              ##STR255## --                                                                                      ##STR256##                                   87  n-C.sub.3 H.sub.7                                                                     ##STR257## --                                                                                      ##STR258##                                   88  C.sub.2 H.sub.5 O                                                                     ##STR259## --                                                                                      ##STR260##                                   89  NC                                                                                    ##STR261## --                                                                                      ##STR262##                                   90  F                                                                                     ##STR263## --                                                                                      ##STR264##                                   91  CH.sub.3                                                                              ##STR265## --                                                                                      ##STR266##                                   92  C.sub.2 H.sub.5                                                                       ##STR267## --                                                                                      ##STR268##                                   93  n-C.sub.3 H.sub.7                                                                     ##STR269## --                                                                                      ##STR270##                                   94  n-C.sub.5 H.sub.11                                                                    ##STR271## --                                                                                      ##STR272##                                   95  n-C.sub.3 H.sub.7                                                                     ##STR273## --                                                                                      ##STR274##                                   96  n-C.sub.3 H.sub.7                                                                     ##STR275## --                                                                                      ##STR276##                                   97  CH.sub.3                                                                              ##STR277## --                                                                                      ##STR278##                                   98  n-C.sub.3 H.sub.7                                                                     ##STR279## --                                                                                      ##STR280##                                   99  CH.sub.3                                                                              ##STR281## --                                                                                      ##STR282##                                  100  n-C.sub.3 H.sub.7                                                                     ##STR283## --                                                                                      ##STR284##                                  101  CH.sub.3                                                                              ##STR285## --                                                                                      ##STR286##                                  102  n-C.sub.3 H.sub.7                                                                     ##STR287## --                                                                                      ##STR288##                                  103  CH.sub.3                                                                              ##STR289##                                                                                ##STR290##                                                                             ##STR291##                                  104  C.sub.2 H.sub.5                                                                       ##STR292##                                                                                ##STR293##                                                                             ##STR294##                                  105  n-C.sub.3 H.sub.7                                                                     ##STR295##                                                                                ##STR296##                                                                             ##STR297##                                  106  n-C.sub.5 H.sub.11                                                                    ##STR298##                                                                                ##STR299##                                                                             ##STR300##                                  107  n-C.sub.3 H.sub.7                                                                     ##STR301##                                                                                ##STR302##                                                                             ##STR303##                                  108  CH.sub.3                                                                              ##STR304## --CO.sub.2 --                                                                           ##STR305##                                  109  C.sub.2 H.sub.5                                                                       ##STR306## --CO.sub.2 --                                                                           ##STR307##                                  110  n-C.sub.3 H.sub.7                                                                     ##STR308## --CO.sub.2 --                                                                           ##STR309##                                  111  n-C.sub.5 H.sub.11                                                                    ##STR310## --CO.sub.2 --                                                                           ##STR311##                                  112  n-C.sub.3 H.sub.7                                                                     ##STR312## --CO.sub.2 --                                                                           ##STR313##                                  113  CH.sub.3                                                                              ##STR314## --                                                                                      ##STR315##                                  114  C.sub.2 H.sub.5                                                                       ##STR316## --                                                                                      ##STR317##                                  115  n-C.sub.3 H.sub.7                                                                     ##STR318## --                                                                                      ##STR319##                                  116  n-C.sub.5 H.sub.11                                                                    ##STR320## --                                                                                      ##STR321##                                  117  n-C.sub.3 H.sub.7                                                                     ##STR322## --                                                                                      ##STR323##                                  118  n-C.sub.3 H.sub.7                                                                     ##STR324## --                                                                                      ##STR325##                                  119  CH.sub.3                                                                              ##STR326## --                                                                                      ##STR327##                                  120  C.sub.2 H.sub.5                                                                       ##STR328## --                                                                                      ##STR329##                                  121  n-C.sub.3 H.sub.7                                                                     ##STR330## --                                                                                      ##STR331##                                  122  n-C.sub.5 H.sub.11                                                                    ##STR332## --                                                                                      ##STR333##                                  123  n-C.sub.3 H.sub.7                                                                     ##STR334## --                                                                                      ##STR335##                                  124  n-C.sub.3 H.sub.7                                                                     ##STR336## --                                                                                      ##STR337##                                  125  n-C.sub.3 H.sub.7                                                                     ##STR338## --                                                                                      ##STR339##                                  126  CH.sub.3                                                                              ##STR340## --                                                                                      ##STR341##                                  127  n-C.sub.3 H.sub.7                                                                     ##STR342## --                                                                                      ##STR343##                                  128  n-C.sub.5 H.sub.11                                                                    ##STR344## --                                                                                      ##STR345##                                  129  n-C.sub.3 H.sub.7                                                                     ##STR346## --                                                                                      ##STR347##                                  130                                                                                 ##STR348##                                                                           ##STR349## --                                                                                      ##STR350##                                  131  CH.sub.3                                                                              ##STR351## --                                                                                      ##STR352##                                  132  C.sub.2 H.sub.5                                                                       ##STR353## --                                                                                      ##STR354##                                  133  n-C.sub.3 H.sub.7                                                                     ##STR355## --                                                                                      ##STR356##                                  134  n-C.sub.5 H.sub.11                                                                    ##STR357## --                                                                                      ##STR358##                                  135  n-C.sub.3 H.sub.7                                                                     ##STR359## --                                                                                      ##STR360##                                  136  NC                                                                                    ##STR361## --                                                                                      ##STR362##                                  137  CH.sub.3                                                                              ##STR363## --                                                                                      ##STR364##                                  138  C.sub.2 H.sub.5                                                                       ##STR365## --                                                                                      ##STR366##                                  139  n-C.sub.3 H.sub.7                                                                     ##STR367## --                                                                                      ##STR368##                                  140  n-C.sub.5 H.sub.11                                                                    ##STR369## --                                                                                      ##STR370##                                  141  n-C.sub.3 H.sub.7                                                                     ##STR371## --                                                                                      ##STR372##                                  142  n-C.sub.3 H.sub.7                                                                     ##STR373## --                                                                                      ##STR374##                                  143  CH.sub.3                                                                              ##STR375## --                                                                                      ##STR376##                                  144  n-C.sub.3 H.sub.7                                                                     ##STR377## --                                                                                      ##STR378##                                  145  CH.sub.3                                                                              ##STR379## --                                                                                      ##STR380##                                  146  n-C.sub.3 H.sub.7                                                                     ##STR381## --                                                                                      ##STR382##                                  147  CH.sub.3                                                                              ##STR383## --                                                                                      ##STR384##                                  148  n-C.sub.3 H.sub.7                                                                     ##STR385## --                                                                                      ##STR386##                                  149  CH.sub.3                                                                              ##STR387##                                                                                ##STR388##                                                                             ##STR389##                                  150  C.sub.2 H.sub.5                                                                       ##STR390##                                                                                ##STR391##                                                                             ##STR392##                                  151  n-C.sub.3 H.sub.7                                                                     ##STR393##                                                                                ##STR394##                                                                             ##STR395##                                  152  n-C.sub.5 H.sub.11                                                                    ##STR396##                                                                                ##STR397##                                                                             ##STR398##                                  153  n-C.sub.3 H.sub.7                                                                     ##STR399##                                                                                ##STR400##                                                                             ##STR401##                                  154  CH.sub.3                                                                              ##STR402## --CO.sub.2 --                                                                           ##STR403##                                  155  C.sub.2 H.sub.5                                                                       ##STR404## --CO.sub.2 --                                                                           ##STR405##                                  156  n-C.sub.3 H.sub.7                                                                     ##STR406## --CO.sub.2 --                                                                           ##STR407##                                  157  n-C.sub.5 H.sub.11                                                                    ##STR408## --CO.sub.2 --                                                                           ##STR409##                                  158  n-C.sub.3 H.sub.7                                                                     ##STR410## --CO.sub.2 --                                                                           ##STR411##                                  159  CH.sub.3                                                                              ##STR412## --                                                                                      ##STR413##                                  160  C.sub.2 H.sub.5                                                                       ##STR414## --                                                                                      ##STR415##                                  161  n-C.sub.3 H.sub.7                                                                     ##STR416## --                                                                                      ##STR417##                                  162  n-C.sub.3 H.sub.7                                                                     ##STR418## --                                                                                      ##STR419##                                  163  n-C.sub.5 H.sub.11                                                                    ##STR420## --                                                                                      ##STR421##                                  164  n-C.sub.3 H.sub.7                                                                     ##STR422## --                                                                                      ##STR423##                                  165  CH.sub.3                                                                              ##STR424## --                                                                                      ##STR425##                                  166  C.sub.2 H.sub.5                                                                       ##STR426## --                                                                                      ##STR427##                                  167  n-C.sub.3 H.sub.7                                                                     ##STR428## --                                                                                      ##STR429##                                  168  n-C.sub.5 H.sub.11                                                                    ##STR430## --                                                                                      ##STR431##                                  169  n-C.sub.3 H.sub.7                                                                     ##STR432## --                                                                                      ##STR433##                                  170  n-C.sub.3 H.sub.7                                                                     ##STR434## --                                                                                      ##STR435##                                  171  n-C.sub.3 H.sub.7                                                                     ##STR436## --                                                                                      ##STR437##                                  172  CH.sub.3                                                                              ##STR438## --                                                                                      ##STR439##                                  173  C.sub.2 H.sub.5                                                                       ##STR440## --                                                                                      ##STR441##                                  174  n-C.sub.3 H.sub.7                                                                     ##STR442## --                                                                                      ##STR443##                                  175  n-C.sub.5 H.sub.11                                                                    ##STR444## --                                                                                      ##STR445##                                  176  n-C.sub.3 H.sub.7                                                                     ##STR446## --                                                                                      ##STR447##                                  177                                                                                 ##STR448##                                                                           ##STR449## --                                                                                      ##STR450##                                  178                                                                                 ##STR451##                                                                           ##STR452## --                                                                                      ##STR453##                                  __________________________________________________________________________    m = 0, n = p = 1                                                              No.  B.sub.3      A.sub.4      G                                              __________________________________________________________________________     82  --                                                                                          ##STR454##                                                                                 ##STR455##                                     83  --                                                                                          ##STR456##                                                                                 ##STR457##                                     84  --                                                                                          ##STR458##                                                                                 ##STR459##                                     85  --                                                                                          ##STR460##                                                                                 ##STR461##                                     86  --                                                                                          ##STR462##                                                                                 ##STR463##                                     87  --                                                                                          ##STR464##                                                                                 ##STR465##                                     88  --                                                                                          ##STR466##                                                                                 ##STR467##                                     89  --                                                                                          ##STR468##                                                                                 ##STR469##                                     90  --                                                                                          ##STR470##                                                                                 ##STR471##                                     91  --                                                                                          ##STR472##                                                                                 ##STR473##                                     92  --                                                                                          ##STR474##                                                                                 ##STR475##                                     93  --                                                                                          ##STR476##                                                                                 ##STR477##                                     94  --                                                                                          ##STR478##                                                                                 ##STR479##                                     95  --                                                                                          ##STR480##                                                                                 ##STR481##                                     96  --                                                                                          ##STR482##                                                                                 ##STR483##                                     97  OCH.sub.2                                                                                   ##STR484##                                                                                 ##STR485##                                     98  OCH.sub.2                                                                                   ##STR486##                                                                                 ##STR487##                                     99  CH.sub.2 O                                                                                  ##STR488##                                                                                 ##STR489##                                    100  CH.sub.2 O                                                                                  ##STR490##                                                                                 ##STR491##                                    101                                                                                 ##STR492##                                                                                 ##STR493##                                                                                 ##STR494##                                    102                                                                                 ##STR495##                                                                                 ##STR496##                                                                                 ##STR497##                                    103  --                                                                                          ##STR498##                                                                                 ##STR499##                                    104  --                                                                                          ##STR500##                                                                                 ##STR501##                                    105  --                                                                                          ##STR502##                                                                                 ##STR503##                                    106  --                                                                                          ##STR504##                                                                                 ##STR505##                                    107  --                                                                                          ##STR506##                                                                                 ##STR507##                                    108  --                                                                                          ##STR508##                                                                                 ##STR509##                                    109  --                                                                                          ##STR510##                                                                                 ##STR511##                                    110  --                                                                                          ##STR512##                                                                                 ##STR513##                                    111  --                                                                                          ##STR514##                                                                                 ##STR515##                                    112  --                                                                                          ##STR516##                                                                                 ##STR517##                                    113  --                                                                                          ##STR518##                                                                                 ##STR519##                                    114  --                                                                                          ##STR520##                                                                                 ##STR521##                                    115  --                                                                                          ##STR522##                                                                                 ##STR523##                                    116  --                                                                                          ##STR524##                                                                                 ##STR525##                                    117  --                                                                                          ##STR526##                                                                                 ##STR527##                                    118  --                                                                                          ##STR528##                                                                                 ##STR529##                                    119                                                                                 ##STR530##                                                                                 ##STR531##                                                                                 ##STR532##                                    120                                                                                 ##STR533##                                                                                 ##STR534##                                                                                 ##STR535##                                    121                                                                                 ##STR536##                                                                                 ##STR537##                                                                                 ##STR538##                                    122                                                                                 ##STR539##                                                                                 ##STR540##                                                                                 ##STR541##                                    123                                                                                 ##STR542##                                                                                 ##STR543##                                                                                 ##STR544##                                    124  CH.sub.2 O                                                                                  ##STR545##                                                                                 ##STR546##                                    125                                                                                 ##STR547##                                                                                 ##STR548##                                                                                 ##STR549##                                    126                                                                                 ##STR550##                                                                                 ##STR551##                                                                                 ##STR552##                                    127                                                                                 ##STR553##                                                                                 ##STR554##                                                                                 ##STR555##                                    128                                                                                 ##STR556##                                                                                 ##STR557##                                                                                 ##STR558##                                    129                                                                                 ##STR559##                                                                                 ##STR560##                                                                                 ##STR561##                                    130  --                                                                                          ##STR562##                                                                                 ##STR563##                                    131  --                                                                                          ##STR564##                                                                                 ##STR565##                                    132  --                                                                                          ##STR566##                                                                                 ##STR567##                                    133  --                                                                                          ##STR568##                                                                                 ##STR569##                                    134  --                                                                                          ##STR570##                                                                                 ##STR571##                                    135  --                                                                                          ##STR572##                                                                                 ##STR573##                                    136  --                                                                                          ##STR574##                                                                                 ##STR575##                                    137  --                                                                                          ##STR576##                                                                                 ##STR577##                                    138  --                                                                                          ##STR578##                                                                                 ##STR579##                                    139  --                                                                                          ##STR580##                                                                                 ##STR581##                                    140  --                                                                                          ##STR582##                                                                                 ##STR583##                                    141  --                                                                                          ##STR584##                                                                                 ##STR585##                                    142  --                                                                                          ##STR586##                                                                                 ##STR587##                                    143  OCH.sub.2                                                                                   ##STR588##                                                                                 ##STR589##                                    144  OCH.sub.2                                                                                   ##STR590##                                                                                 ##STR591##                                    145  CH.sub.2 O                                                                                  ##STR592##                                                                                 ##STR593##                                    146  CH.sub.2 O                                                                                  ##STR594##                                                                                 ##STR595##                                    147                                                                                 ##STR596##                                                                                 ##STR597##                                                                                 ##STR598##                            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                     152  --                                                                                          ##STR608##                                                                                 ##STR609##                                    153  --                                                                                          ##STR610##                                                                                 ##STR611##                                    154  --                                                                                          ##STR612##                                                                                 ##STR613##                                    155  --                                                                                          ##STR614##                                                                                 ##STR615##                                    156  --                                                                                          ##STR616##                                                                                 ##STR617##                                    157  --                                                                                          ##STR618##                                                                                 ##STR619##                                    158  --                                                                                          ##STR620##                                                                                 ##STR621##                                    159  --                                                                                          ##STR622##                                                                                 ##STR623##                                    160  --                                                                                          ##STR624##                                                                                 ##STR625##                                    161  --                                                                                          ##STR626##                                                                                 ##STR627##                                    162  --                                                                                          ##STR628##                                                                                 ##STR629##                                    163  --                                                                                          ##STR630##                                                                                 ##STR631##                                    164  --                                                                                          ##STR632##                                                                                 ##STR633##                                    165                                                                                 ##STR634##                                                                                 ##STR635##                                                                                 ##STR636##                                    166                                                                                 ##STR637##                                                                                 ##STR638##                                                                                 ##STR639##                                    167                                                                                 ##STR640##                                                                                 ##STR641##                                                                                 ##STR642##                                    168                                                                                 ##STR643##                                                                                 ##STR644##                                                                                 ##STR645##                                    169                                                                                 ##STR646##                                                                                 ##STR647##                                                                                 ##STR648##                                    170  CH.sub.2 O                                                                                  ##STR649##                                                                                 ##STR650##                                    171                                                                                 ##STR651##                                                                                 ##STR652##                                                                                 ##STR653##                                    172                                                                                 ##STR654##                                                                                 ##STR655##                                                                                 ##STR656##                                    173                                                                                 ##STR657##                                                                                 ##STR658##                                                                                 ##STR659##                                    174                                                                                 ##STR660##                                                                                 ##STR661##                                                                                 ##STR662##                                    175                                                                                 ##STR663##                                                                                 ##STR664##                                                                                 ##STR665##                                    176                                                                                 ##STR666##                                                                                 ##STR667##                                                                                 ##STR668##                                    177  --                                                                                          ##STR669##                                                                                 ##STR670##                                    178                                                                                 ##STR671##                                                                                 ##STR672##                                                                                 ##STR673##                                    __________________________________________________________________________    m = n = p = 1                                                                 No. R     A.sub.1    B.sub.1                                                                          A.sub.2    B.sub.2                                    __________________________________________________________________________    179 CH.sub.3                                                                             ##STR674##                                                                              --                                                                                ##STR675##                                                                              --                                         180 C.sub.2 H.sub.5                                                                      ##STR676##                                                                              --                                                                                ##STR677##                                                                              --                                         181 n-C.sub.3 H.sub.7                                                                    ##STR678##                                                                              --                                                                                ##STR679##                                                                              --                                         182 n-C.sub.5 H.sub.11                                                                   ##STR680##                                                                              --                                                                                ##STR681##                                                                              --                                         183 n-C.sub.3 H.sub.7                                                                    ##STR682##                                                                              --                                                                                ##STR683##                                                                              --                                         184 CH.sub.3                                                                             ##STR684##                                                                              --                                                                                ##STR685##                                                                              --                                         185 C.sub.2 H.sub.5                                                                      ##STR686##                                                                              --                                                                                ##STR687##                                                                              --                                         186 n-C.sub.3 H.sub.7                                                                    ##STR688##                                                                              --                                                                                ##STR689##                                                                              --                                         187 n-C.sub.5 H.sub.11                                                                   ##STR690##                                                                              --                                                                                ##STR691##                                                                              --                                         188 n-C.sub.3 H.sub.7                                                                    ##STR692##                                                                              --                                                                                ##STR693##                                                                              --                                         189                                                                                ##STR694##                                                                          ##STR695##                                                                              --                                                                                ##STR696##                                                                              --                                         190 CH.sub.3                                                                             ##STR697##                                                                              --                                                                                ##STR698##                                                                              --                                         191 C.sub.2 H.sub.5                                                                      ##STR699##                                                                              --                                                                                ##STR700##                                                                              --                                         192 n-C.sub.3 H.sub.7                                                                    ##STR701##                                                                              --                                                                                ##STR702##                                                                              --                                         193 n-C.sub.5 H.sub.11                                                                   ##STR703##                                                                              --                                                                                ##STR704##                                                                              --                                         194 n-C.sub.3 H.sub.7                                                                    ##STR705##                                                                              --                                                                                ##STR706##                                                                              --                                         195                                                                                ##STR707##                                                                          ##STR708##                                                                              --                                                                                ##STR709##                                                                              --                                         196 CH.sub.3                                                                             ##STR710##                                                                              --                                                                                ##STR711##                                                                               ##STR712##                                197 C.sub.2 H.sub.5                                                                      ##STR713##                                                                              --                                                                                ##STR714##                                                                               ##STR715##                                198 n-C.sub.3 H.sub.7                                                                    ##STR716##                                                                              --                                                                                ##STR717##                                                                               ##STR718##                                199 n-C.sub.5 H.sub.11                                                                   ##STR719##                                                                              --                                                                                ##STR720##                                                                               ##STR721##                                200 n-C.sub.3 H.sub.7                                                                    ##STR722##                                                                              --                                                                                ##STR723##                                                                               ##STR724##                                201 n-C.sub.3 H.sub.7                                                                    ##STR725##                                                                              --                                                                                ##STR726##                                                                               ##STR727##                                202                                                                                ##STR728##                                                                          ##STR729##                                                                              --                                                                                ##STR730##                                                                               ##STR731##                                203 CH.sub.3                                                                             ##STR732##                                                                              --                                                                                ##STR733##                                                                              --                                         204 C.sub.2 H.sub.5                                                                      ##STR734##                                                                              --                                                                                ##STR735##                                                                              --                                         205 n-C.sub.3 H.sub.7                                                                    ##STR736##                                                                              --                                                                                ##STR737##                                                                              --                                         206 n-C.sub.3 H.sub.7                                                                    ##STR738##                                                                              --                                                                                ##STR739##                                                                              --                                         207 n-C.sub.5 H.sub.11                                                                   ##STR740##                                                                              --                                                                                ##STR741##                                                                              --                                         208 C.sub.2 H.sub.5 O                                                                    ##STR742##                                                                              --                                                                                ##STR743##                                                                              --                                         209                                                                                ##STR744##                                                                          ##STR745##                                                                              --                                                                                ##STR746##                                                                              --                                         210 NC                                                                                   ##STR747##                                                                              --                                                                                ##STR748##                                                                              --                                         211 F                                                                                    ##STR749##                                                                              --                                                                                ##STR750##                                                                              --                                         212 CH.sub.3                                                                             ##STR751##                                                                              --                                                                                ##STR752##                                                                              --                                         213 C.sub.2 H.sub.5                                                                      ##STR753##                                                                              --                                                                                ##STR754##                                                                              --                                         214 n-C.sub.3 H.sub.7                                                                    ##STR755##                                                                              --                                                                                ##STR756##                                                                              --                                         215 n-C.sub.5 H.sub.11                                                                   ##STR757##                                                                              --                                                                                ##STR758##                                                                              --                                         216 n-C.sub.3 H.sub.7                                                                    ##STR759##                                                                              --                                                                                ##STR760##                                                                              --                                         217 CH.sub.3                                                                             ##STR761##                                                                              --                                                                                ##STR762##                                                                              --                                         218 C.sub.2 H.sub.5                                                                      ##STR763##                                                                              --                                                                                ##STR764##                                                                              --                                         219 n-C.sub.3 H.sub.7                                                                    ##STR765##                                                                              --                                                                                ##STR766##                                                                              --                                         220 n-C.sub.5 H.sub.11                                                                   ##STR767##                                                                              --                                                                                ##STR768##                                                                              --                                         221 n-C.sub.3 H.sub.7                                                                    ##STR769##                                                                              --                                                                                ##STR770##                                                                              --                                         222                                                                                ##STR771##                                                                          ##STR772##                                                                              --                                                                                ##STR773##                                                                              --                                         223 CH.sub.3                                                                             ##STR774##                                                                              --                                                                                ##STR775##                                                                              --                                         224 C.sub.2 H.sub.5                                                                      ##STR776##                                                                              --                                                                                ##STR777##                                                                              --                                         225 n-C.sub.3 H.sub.7                                                                    ##STR778##                                                                              --                                                                                ##STR779##                                                                              --                                         226 n-C.sub.5 H.sub.11                                                                   ##STR780##                                                                              --                                                                                ##STR781##                                                                              --                                         227 n-C.sub.3 H.sub.7                                                                    ##STR782##                                                                              --                                                                                ##STR783##                                                                              --                                         228                                                                                ##STR784##                                                                          ##STR785##                                                                              --                                                                                ##STR786##                                                                              --                                         229 CH.sub.3                                                                             ##STR787##                                                                              --                                                                                ##STR788##                                                                               ##STR789##                                230 C.sub.2 H.sub.5                                                                      ##STR790##                                                                              --                                                                                ##STR791##                                                                               ##STR792##                                231 n-C.sub.3 H.sub.7                                                                    ##STR793##                                                                              --                                                                                ##STR794##                                                                               ##STR795##                                232 n-C.sub.5 H.sub.11                                                                   ##STR796##                                                                              --                                                                                ##STR797##                                                                               ##STR798##                                233 n-C.sub.3 H.sub.7                                                                    ##STR799##                                                                              --                                                                                ##STR800##                                                                               ##STR801##                                234 n-C.sub.3 H.sub.7                                                                    ##STR802##                                                                              --                                                                                ##STR803##                                                                               ##STR804##                                235                                                                                ##STR805##                                                                          ##STR806##                                                                              --                                                                                ##STR807##                                                                               ##STR808##                                236 CH.sub.3                                                                             ##STR809##                                                                              --                                                                                ##STR810##                                                                              --                                         237 C.sub.2 H.sub.5                                                                      ##STR811##                                                                              --                                                                                ##STR812##                                                                              --                                         238 n-C.sub.3 H.sub.7                                                                    ##STR813##                                                                              --                                                                                ##STR814##                                                                              --                                         239 n-C.sub.3 H.sub.7                                                                    ##STR815##                                                                              --                                                                                ##STR816##                                                                              --                                         240 n-C.sub.5 H.sub.11                                                                   ##STR817##                                                                              --                                                                                ##STR818##                                                                              --                                         241 C.sub.2 H.sub.5 O                                                                    ##STR819##                                                                              --                                                                                ##STR820##                                                                              --                                         242                                                                                ##STR821##                                                                          ##STR822##                                                                              --                                                                                ##STR823##                                                                              --                                         243 NC                                                                                   ##STR824##                                                                              --                                                                                ##STR825##                                                                              --                                         244 F                                                                                    ##STR826##                                                                              --                                                                                ##STR827##                                                                              --                                         __________________________________________________________________________    m = n = p = 1                                                                 No.                                                                              A.sub.3    B.sub.3                                                                              A.sub.4    G                                             __________________________________________________________________________    179                                                                               ##STR828##                                                                              --                                                                                    ##STR829##                                                                               ##STR830##                                   180                                                                               ##STR831##                                                                              --                                                                                    ##STR832##                                                                               ##STR833##                                   181                                                                               ##STR834##                                                                              --                                                                                    ##STR835##                                                                               ##STR836##                                   182                                                                               ##STR837##                                                                              --                                                                                    ##STR838##                                                                               ##STR839##                                   183                                                                               ##STR840##                                                                              --                                                                                    ##STR841##                                                                               ##STR842##                                   184                                                                               ##STR843##                                                                               ##STR844##                                                                           ##STR845##                                                                               ##STR846##                                   185                                                                               ##STR847##                                                                               ##STR848##                                                                           ##STR849##                                                                               ##STR850##                                   186                                                                               ##STR851##                                                                               ##STR852##                                                                           ##STR853##                                                                               ##STR854##                                   187                                                                               ##STR855##                                                                               ##STR856##                                                                           ##STR857##                                                                               ##STR858##                                   188                                                                               ##STR859##                                                                               ##STR860##                                                                           ##STR861##                                                                               ##STR862##                                   189                                                                               ##STR863##                                                                               ##STR864##                                                                           ##STR865##                                                                               ##STR866##                                   190                                                                               ##STR867##                                                                              --                                                                                    ##STR868##                                                                               ##STR869##                                   191                                                                               ##STR870##                                                                              --                                                                                    ##STR871##                                                                               ##STR872##                                   192                                                                               ##STR873##                                                                              --                                                                                    ##STR874##                                                                               ##STR875##                                   193                                                                               ##STR876##                                                                              --                                                                                    ##STR877##                                                                               ##STR878##                                   194                                                                               ##STR879##                                                                              --                                                                                    ##STR880##                                                                               ##STR881##                                   195                                                                               ##STR882##                                                                              --                                                                                    ##STR883##                                                                               ##STR884##                                   196                                                                               ##STR885##                                                                              --                                                                                    ##STR886##                                                                               ##STR887##                                   197                                                                               ##STR888##                                                                              --                                                                                    ##STR889##                                                                               ##STR890##                                   198                                                                               ##STR891##                                                                              --                                                                                    ##STR892##                                                                               ##STR893##                                   199                                                                               ##STR894##                                                                              --                                                                                    ##STR895##                                                                               ##STR896##                                   200                                                                               ##STR897##                                                                              --                                                                                    ##STR898##                                                                               ##STR899##                                   201                                                                               ##STR900##                                                                              --                                                                                    ##STR901##                                                                               ##STR902##                                   202                                                                               ##STR903##                                                                              --                                                                                    ##STR904##                                                                               ##STR905##                                   203                                                                               ##STR906##                                                                              --                                                                                    ##STR907##                                                                               ##STR908##                                   204                                                                               ##STR909##                                                                              --                                                                                    ##STR910##                                                                               ##STR911##                                   205                                                                               ##STR912##                                                                              --                                                                                    ##STR913##                                                                               ##STR914##                                   206                                                                               ##STR915##                                                                              --                                                                                    ##STR916##                                                                               ##STR917##                                   207                                                                               ##STR918##                                                                              --                                                                                    ##STR919##                                                                               ##STR920##                                   208                                                                               ##STR921##                                                                              --                                                                                    ##STR922##                                                                               ##STR923##                                   209                                                                               ##STR924##                                                                              --                                                                                    ##STR925##                                                                               ##STR926##                                   210                                                                               ##STR927##                                                                              --                                                                                    ##STR928##                                                                               ##STR929##                                   211                                                                               ##STR930##                                                                              --                                                                                    ##STR931##                                                                               ##STR932##                                   212                                                                               ##STR933##                                                                              --                                                                                    ##STR934##                                                                               ##STR935##                                   213                                                                               ##STR936##                                                                              --                                                                                    ##STR937##                                                                               ##STR938##                                   214                                                                               ##STR939##                                                                              --                                                                                    ##STR940##                                                                               ##STR941##                                   215                                                                               ##STR942##                                                                              --                                                                                    ##STR943##                                                                               ##STR944##                                   216                                                                               ##STR945##                                                                              --                                                                                    ##STR946##                                                                               ##STR947##                                   217                                                                               ##STR948##                                                                               ##STR949##                                                                           ##STR950##                                                                               ##STR951##                                   218                                                                               ##STR952##                                                                               ##STR953##                                                                           ##STR954##                                                                               ##STR955##                                   219                                                                               ##STR956##                                                                               ##STR957##                                                                           ##STR958##                                                                               ##STR959##                                   220                                                                               ##STR960##                                                                               ##STR961##                                                                           ##STR962##                                                                               ##STR963##                                   221                                                                               ##STR964##                                                                               ##STR965##                                                                           ##STR966##                                                                               ##STR967##                                   222                                                                               ##STR968##                                                                               ##STR969##                                                                           ##STR970##                                                                               ##STR971##                                   223                                                                               ##STR972##                                                                              --                                                                                    ##STR973##                                                                               ##STR974##                                   224                                                                               ##STR975##                                                                              --                                                                                    ##STR976##                                                                               ##STR977##                                   225                                                                               ##STR978##                                                                              --                                                                                    ##STR979##                                                                               ##STR980##                                   226                                                                               ##STR981##                                                                              --                                                                                    ##STR982##                                                                               ##STR983##                                   227                                                                               ##STR984##                                                                              --                                                                                    ##STR985##                                                                               ##STR986##                                   228                                                                               ##STR987##                                                                              --                                                                                    ##STR988##                                                                               ##STR989##                                   229                                                                               ##STR990##                                                                              --                                                                                    ##STR991##                                                                               ##STR992##                                   230                                                                               ##STR993##                                                                              --                                                                                    ##STR994##                                                                               ##STR995##                                   231                                                                               ##STR996##                                                                              --                                                                                    ##STR997##                                                                               ##STR998##                                   232                                                                               ##STR999##                                                                              --                                                                                    ##STR1000##                                                                              ##STR1001##                                  233                                                                               ##STR1002##                                                                             --                                                                                    ##STR1003##                                                                              ##STR1004##                                  234                                                                               ##STR1005##                                                                             --                                                                                    ##STR1006##                                                                              ##STR1007##                                  235                                                                               ##STR1008##                                                                             --                                                                                    ##STR1009##                                                                              ##STR1010##                                  236                                                                               ##STR1011##                                                                             --                                                                                    ##STR1012##                                                                              ##STR1013##                                  237                                                                               ##STR1014##                                                                             --                                                                                    ##STR1015##                                                                              ##STR1016##                                  238                                                                               ##STR1017##                                                                             --                                                                                    ##STR1018##                                                                              ##STR1019##                                  239                                                                               ##STR1020##                                                                             --                                                                                    ##STR1021##                                                                              ##STR1022##                                  240                                                                               ##STR1023##                                                                             --                                                                                    ##STR1024##                                                                              ##STR1025##                                  241                                                                               ##STR1026##                                                                             --                                                                                    ##STR1027##                                                                              ##STR1028##                                  242                                                                               ##STR1029##                                                                             --                                                                                    ##STR1030##                                                                              ##STR1031##                                  243                                                                               ##STR1032##                                                                             --                                                                                    ##STR1033##                                                                              ##STR1034##                                  244                                                                               ##STR1035##                                                                             --                                                                                    ##STR1036##                                                                              ##STR1037##                                  __________________________________________________________________________

EXAMPLE 10

Preparation of1-(4-cyano-1-butyne-3-ene-1-yl)-4-(2-(trans-4-propylcyclohexyl)ethylbenzene(Compound No. 250)

To dichlorobistriphenylphosphine palladium and copper iodide was addedto suspend diethylamine, and then 1,2-dichloroethylene was added theretowhile being stirred, and it was further stirred for 15 minutes. To thereaction liquid was added by drops a solution of1-ethynyl-4-(2-(trans-4-propylcyclohexyl)ethylbenzene in diehtylamine,and further stirred at room temperature for 3 hours. After finishing ofthe reaction, water was added to the solution and extracted withtoluene. The organic layer thus obtained was washed with water, driedover anhydrous magnesium sulfate, and then concentrated under a reducedpressure to obtain a brown oily product.

After this product was purified by using silica gel columnchromatography, it was recrystallized from ethanol to obtain whitecrystals of1-(4-chloro-1-butyne-3-ene-1-yl)-4-(2-(trans-4-propylcyclohexyl)ethylbenzene.

This product and copper cyanide were dissolved in N-methylpyrrolidoneand then stirred under heated reflux condition for 3 hours. After thefinishing of the reaction, a solution of iron (II) chloride in 6Nhydrochloric acid was added to the solution and further stirred for 30minutes. After this solution was filtrated through Celite (filtermedium), and undissolved matters were separated, it was extracted withtoluene. After the organic layer was washed with water, it was driedover anhydrous magnesium sulfate, and then concentrated under a reducedpressure to obtain a brown oily product. This product was purified andisolated by using silica gel column chromatography to obtain the subjectcompound.

C.43.6.N.147.3.I.

EXAMPLE 11

Preparation of1-(4-cyano-1-butyne-3-ene-1-yl)-4-(trans-4-vinylcyclohexyl)benzene(Compound No. 252).

To dichlorobistriphenylphosphine palladium and copper iodide was addedto suspend diethylamine, and then 1,2-dichloroethylene was added theretowhile being stirred, and it was further stirred for 15 minutes.

To the reaction liquid was added by drops a solution of1-ethynyl-4-(trans-4-vinylcyclohexyl)benzene in diehtylamine, andfurther stirred at room temperature for 3 hours. After finishing of thereaction, water was added to the solution and extracted with toluene.The organic layer thus obtained was washed with water, dried overanhydrous magnesium sulfate, and then concentrated under a reducedpressure to obtain a brown oily product. After this product was purifiedby using silica gel column chromatography, it was recrystallized fromethanol to obtain white crystals of1-(4-chloro-1-butyne-3-ene-1-yl)-4(trans-4-vinylcyclohexyl)benzene.

This product and copper cyanide were dissolved in N-methylpyrrolidoneand then stirred under heated reflux condition for 3 hours. Afterfinishing of the reaction, a solution of iron (II) chloride in 6Nhydrochloric acid was added thereto and further stirred for 30 minutes.After this solution was filtrated through Celite (filter medium), andundissolved matters were separated, it was extracted with toluene. Afterthe organic layer was washed with water, it was dried over anhydrousmagnesium sulfate, and then concentrated under a reduced pressure toobtain a brown oily product. This product was purified and isolated byusing silica gel column chromatography to obtain the subject compound.

Based on the descriptions in Examples 10 and 11, the following compoundsof No. 245 to No. 354 can be prepared.

In the following, compounds obtained in Examples 10 and 11 are describedagain.

    __________________________________________________________________________    m = 1, n = p = 0                                                              No.                                                                              R        A.sub.1                                                                             B.sub.1    A.sub.4                                                                             G                                          __________________________________________________________________________    245                                                                              CH.sub.3                                                                                ##STR1038##                                                                        --                                                                                        ##STR1039##                                                                         ##STR1040##                               246                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1041##                                                                        --                                                                                        ##STR1042##                                                                         ##STR1043##                               247                                                                              n-C.sub.3 H.sub.7                                                                       ##STR1044##                                                                        --                                                                                        ##STR1045##                                                                         ##STR1046##                               248                                                                              CH.sub.3 OCH.sub.2                                                                      ##STR1047##                                                                         ##STR1048##                                                                              ##STR1049##                                                                         ##STR1050##                               249                                                                              n-C.sub.3 H.sub.7                                                                       ##STR1051##                                                                         ##STR1052##                                                                              ##STR1053##                                                                         ##STR1054##                               250                                                                              n-C.sub.5 H.sub.11                                                                      ##STR1055##                                                                         ##STR1056##                                                                              ##STR1057##                                                                         ##STR1058##                               251                                                                              n-C.sub.7 H.sub.15                                                                      ##STR1059##                                                                         ##STR1060##                                                                              ##STR1061##                                                                         ##STR1062##                               252                                                                              CH.sub.2 ═CH                                                                        ##STR1063##                                                                        --                                                                                        ##STR1064##                                                                         ##STR1065##                               253                                                                              CH.sub.2 ═CH--(CH.sub.2).sub.2                                                      ##STR1066##                                                                        --                                                                                        ##STR1067##                                                                         ##STR1068##                               254                                                                              CH.sub.2 FCH.sub.2 CH═CH                                                            ##STR1069##                                                                        --                                                                                        ##STR1070##                                                                         ##STR1071##                               255                                                                              CH.sub.3                                                                                ##STR1072##                                                                        --                                                                                        ##STR1073##                                                                         ##STR1074##                               256                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1075##                                                                        --                                                                                        ##STR1076##                                                                         ##STR1077##                               257                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1078##                                                                        --                                                                                        ##STR1079##                                                                         ##STR1080##                               258                                                                              CH.sub.3 OCH.sub.2                                                                      ##STR1081##                                                                        --                                                                                        ##STR1082##                                                                         ##STR1083##                               259                                                                              n-C.sub.3 H.sub.7                                                                       ##STR1084##                                                                        --                                                                                        ##STR1085##                                                                         ##STR1086##                               260                                                                              n-C.sub.5 H.sub.11                                                                      ##STR1087##                                                                        --                                                                                        ##STR1088##                                                                         ##STR1089##                               261                                                                              n-C.sub.7 H.sub.15                                                                      ##STR1090##                                                                        --                                                                                        ##STR1091##                                                                         ##STR1092##                               262                                                                              CH.sub.2 ═CH                                                                        ##STR1093##                                                                        --                                                                                        ##STR1094##                                                                         ##STR1095##                               263                                                                              CH.sub.2 ═CH--(CH.sub.2).sub.2                                                      ##STR1096##                                                                        --                                                                                        ##STR1097##                                                                         ##STR1098##                               264                                                                              CH.sub.2 FCH.sub.2 CH═CH                                                            ##STR1099##                                                                        --                                                                                        ##STR1100##                                                                         ##STR1101##                               265                                                                              CH.sub.3                                                                                ##STR1102##                                                                         ##STR1103##                                                                              ##STR1104##                                                                         ##STR1105##                               266                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1106##                                                                         ##STR1107##                                                                              ##STR1108##                                                                         ##STR1109##                               267                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1110##                                                                         ##STR1111##                                                                              ##STR1112##                                                                         ##STR1113##                               268                                                                              CH.sub.3 OCH.sub.2                                                                      ##STR1114##                                                                         ##STR1115##                                                                              ##STR1116##                                                                         ##STR1117##                               269                                                                              n-C.sub.3 H.sub.7                                                                       ##STR1118##                                                                         ##STR1119##                                                                              ##STR1120##                                                                         ##STR1121##                               270                                                                              n-C.sub.5 H.sub.11                                                                      ##STR1122##                                                                         ##STR1123##                                                                              ##STR1124##                                                                         ##STR1125##                               271                                                                              n-C.sub.7 H.sub.15                                                                      ##STR1126##                                                                         ##STR1127##                                                                              ##STR1128##                                                                         ##STR1129##                               272                                                                              CH.sub.2 ═CH                                                                        ##STR1130##                                                                         ##STR1131##                                                                              ##STR1132##                                                                         ##STR1133##                               273                                                                              CH.sub.2 ═CH--(CH.sub.2).sub.2                                                      ##STR1134##                                                                         ##STR1135##                                                                              ##STR1136##                                                                         ##STR1137##                               274                                                                              CH.sub.2 FCH.sub.2 CH═CH                                                            ##STR1138##                                                                         ##STR1139##                                                                              ##STR1140##                                                                         ##STR1141##                               275                                                                              CH.sub.3                                                                                ##STR1142##                                                                         ##STR1143##                                                                              ##STR1144##                                                                         ##STR1145##                               276                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1146##                                                                         ##STR1147##                                                                              ##STR1148##                                                                         ##STR1149##                               277                                                                              CH.sub.3 CH.sub.2                                                                       ##STR1150##                                                                         ##STR1151##                                                                              ##STR1152##                                                                         ##STR1153##                               278                                                                              CH.sub.3 OCH.sub.2                                                                      ##STR1154##                                                                         ##STR1155##                                                                              ##STR1156##                                                                         ##STR1157##                               279                                                                              n-C.sub.3 H.sub.7                                                                       ##STR1158##                                                                         ##STR1159##                                                                              ##STR1160##                                                                         ##STR1161##                               280                                                                              n-C.sub.5 H.sub.11                                                                      ##STR1162##                                                                         ##STR1163##                                                                              ##STR1164##                                                                         ##STR1165##                               281                                                                              n-C.sub.7 H.sub.15                                                                      ##STR1166##                                                                         ##STR1167##                                                                              ##STR1168##                                                                         ##STR1169##                               282                                                                              CH.sub.2 ═CH                                                                        ##STR1170##                                                                         ##STR1171##                                                                              ##STR1172##                                                                         ##STR1173##                               283                                                                              CH.sub.2 ═CH--(CH.sub.2).sub.2                                                      ##STR1174##                                                                         ##STR1175##                                                                              ##STR1176##                                                                         ##STR1177##                               284                                                                              CH.sub.2 FCH.sub.2 CH═CH                                                            ##STR1178##                                                                         ##STR1179##                                                                              ##STR1180##                                                                         ##STR1181##                               __________________________________________________________________________    m = n = 1, p = 0                                                              No.   R          A1       B.sub.1      A2                                     __________________________________________________________________________    285   CH.sub.3                                                                                  ##STR1182##                                                                           --                                                                                          ##STR1183##                           286   CH.sub.3 CH.sub.2                                                                         ##STR1184##                                                                           --                                                                                          ##STR1185##                           287   CH.sub.3 CH.sub.2                                                                         ##STR1186##                                                                           --                                                                                          ##STR1187##                           288   CH.sub.3 OCH.sub.2                                                                        ##STR1188##                                                                           --                                                                                          ##STR1189##                           289   n-C.sub.3 H.sub.7                                                                         ##STR1190##                                                                           --                                                                                          ##STR1191##                           290   n-C.sub.5 H.sub.11                                                                        ##STR1192##                                                                           --                                                                                          ##STR1193##                           291   n-C.sub.7 H.sub.15                                                                        ##STR1194##                                                                           --                                                                                          ##STR1195##                           292   CH.sub.2 ═CH                                                                          ##STR1196##                                                                           --                                                                                          ##STR1197##                           293   CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1198##                                                                           --                                                                                          ##STR1199##                           294   CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1200##                                                                           --                                                                                          ##STR1201##                           295   CH.sub.3                                                                                  ##STR1202##                                                                            ##STR1203##                                                                                ##STR1204##                           296   CH.sub.3 CH.sub.2                                                                         ##STR1205##                                                                            ##STR1206##                                                                                ##STR1207##                           297   CH.sub.3 CH.sub.2                                                                         ##STR1208##                                                                            ##STR1209##                                                                                ##STR1210##                           298   CH.sub.3 OCH.sub.2                                                                        ##STR1211##                                                                            ##STR1212##                                                                                ##STR1213##                           299   n-C.sub.3 H.sub.7                                                                         ##STR1214##                                                                            ##STR1215##                                                                                ##STR1216##                           300   n-C.sub.5 H.sub.11                                                                        ##STR1217##                                                                            ##STR1218##                                                                                ##STR1219##                           301   n-C.sub.7 H.sub.15                                                                        ##STR1220##                                                                            ##STR1221##                                                                                ##STR1222##                           302   CH.sub.2 ═CH                                                                          ##STR1223##                                                                            ##STR1224##                                                                                ##STR1225##                           303   CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1226##                                                                            ##STR1227##                                                                                ##STR1228##                           304   CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1229##                                                                            ##STR1230##                                                                                ##STR1231##                           305   CH.sub.3                                                                                  ##STR1232##                                                                           --                                                                                          ##STR1233##                           306   CH.sub.3 CH.sub.2                                                                         ##STR1234##                                                                           --                                                                                          ##STR1235##                           307   CH.sub.3 CH.sub.2                                                                         ##STR1236##                                                                           --                                                                                          ##STR1237##                           308   CH.sub.3 OCH.sub.2                                                                        ##STR1238##                                                                           --                                                                                          ##STR1239##                           309   n-C.sub.3 H.sub.7                                                                         ##STR1240##                                                                           --                                                                                          ##STR1241##                           310   n-C.sub.5 H.sub.11                                                                        ##STR1242##                                                                           --                                                                                          ##STR1243##                           311   n-C.sub.7 H.sub.15                                                                        ##STR1244##                                                                           --                                                                                          ##STR1245##                           312   CH.sub.2 ═CH                                                                          ##STR1246##                                                                           --                                                                                          ##STR1247##                           313   CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1248##                                                                           --                                                                                          ##STR1249##                           314   CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1250##                                                                           --                                                                                          ##STR1251##                           315   CH.sub.3                                                                                  ##STR1252##                                                                           --                                                                                          ##STR1253##                           316   CH.sub.3 CH.sub.2                                                                         ##STR1254##                                                                           --                                                                                          ##STR1255##                           317   CH.sub.3 CH.sub.2                                                                         ##STR1256##                                                                           --                                                                                          ##STR1257##                           318   CH.sub.3 OCH.sub.2                                                                        ##STR1258##                                                                           --                                                                                          ##STR1259##                           319   n-C.sub.3 H.sub.7                                                                         ##STR1260##                                                                           --                                                                                          ##STR1261##                           320   n-C.sub.5 H.sub.11                                                                        ##STR1262##                                                                           --                                                                                          ##STR1263##                           321   n-C.sub.7 H.sub.15                                                                        ##STR1264##                                                                           --                                                                                          ##STR1265##                           322   CH.sub.2 ═CH                                                                          ##STR1266##                                                                           --                                                                                          ##STR1267##                           323   CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1268##                                                                           --                                                                                          ##STR1269##                           324   CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1270##                                                                            ##STR1271##                                                                                ##STR1272##                           325   CH.sub.3                                                                                  ##STR1273##                                                                           --                                                                                          ##STR1274##                           326   CH.sub.3 CH.sub.2                                                                         ##STR1275##                                                                           --                                                                                          ##STR1276##                           327   CH.sub.3 CH.sub.2                                                                         ##STR1277##                                                                           --                                                                                          ##STR1278##                           328   CH.sub.3 OCH.sub.2                                                                        ##STR1279##                                                                           --                                                                                          ##STR1280##                           329   n-C.sub.3 H.sub.7                                                                         ##STR1281##                                                                           --                                                                                          ##STR1282##                           330   n-C.sub.5 H.sub.11                                                                        ##STR1283##                                                                           --                                                                                          ##STR1284##                           331   n-C.sub.7 H.sub.15                                                                        ##STR1285##                                                                           --                                                                                          ##STR1286##                           332   CH.sub.2 ═CH                                                                          ##STR1287##                                                                           --                                                                                          ##STR1288##                           333   CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1289##                                                                           --                                                                                          ##STR1290##                           334   CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1291##                                                                           --                                                                                          ##STR1292##                           __________________________________________________________________________    m = n = 1, p = 0                                                              No.   B.sub.2        A4        G                                              __________________________________________________________________________    285   --                                                                                            ##STR1293##                                                                             ##STR1294##                                   286   --                                                                                            ##STR1295##                                                                             ##STR1296##                                   287   --                                                                                            ##STR1297##                                                                             ##STR1298##                                   288   --                                                                                            ##STR1299##                                                                             ##STR1300##                                   289   --                                                                                            ##STR1301##                                                                             ##STR1302##                                   290   --                                                                                            ##STR1303##                                                                             ##STR1304##                                   291   --                                                                                            ##STR1305##                                                                             ##STR1306##                                   292   --                                                                                            ##STR1307##                                                                             ##STR1308##                                   293   --                                                                                            ##STR1309##                                                                             ##STR1310##                                   294   --                                                                                            ##STR1311##                                                                             ##STR1312##                                   295   --                                                                                            ##STR1313##                                                                             ##STR1314##                                   296   --                                                                                            ##STR1315##                                                                             ##STR1316##                                   297   --                                                                                            ##STR1317##                                                                             ##STR1318##                                   298   --                                                                                            ##STR1319##                                                                             ##STR1320##                                   299   --                                                                                            ##STR1321##                                                                             ##STR1322##                                   300   --                                                                                            ##STR1323##                                                                             ##STR1324##                                   301   --                                                                                            ##STR1325##                                                                             ##STR1326##                                   302   --                                                                                            ##STR1327##                                                                             ##STR1328##                                   303   --                                                                                            ##STR1329##                                                                             ##STR1330##                                   304   --                                                                                            ##STR1331##                                                                             ##STR1332##                                   305   --                                                                                            ##STR1333##                                                                             ##STR1334##                                   306   --                                                                                            ##STR1335##                                                                             ##STR1336##                                   307   --                                                                                            ##STR1337##                                                                             ##STR1338##                                   308   --                                                                                            ##STR1339##                                                                             ##STR1340##                                   309   --                                                                                            ##STR1341##                                                                             ##STR1342##                                   310   --                                                                                            ##STR1343##                                                                             ##STR1344##                                   311   --                                                                                            ##STR1345##                                                                             ##STR1346##                                   312   --                                                                                            ##STR1347##                                                                             ##STR1348##                                   313   --                                                                                            ##STR1349##                                                                             ##STR1350##                                   314   --                                                                                            ##STR1351##                                                                             ##STR1352##                                   315                                                                                  ##STR1353##                                                                                  ##STR1354##                                                                             ##STR1355##                                   316                                                                                  ##STR1356##                                                                                  ##STR1357##                                                                             ##STR1358##                                   317                                                                                  ##STR1359##                                                                                  ##STR1360##                                                                             ##STR1361##                                   318                                                                                  ##STR1362##                                                                                  ##STR1363##                                                                             ##STR1364##                                   319                                                                                  ##STR1365##                                                                                  ##STR1366##                                                                             ##STR1367##                                   320                                                                                  ##STR1368##                                                                                  ##STR1369##                                                                             ##STR1370##                                   321                                                                                  ##STR1371##                                                                                  ##STR1372##                                                                             ##STR1373##                                   322                                                                                  ##STR1374##                                                                                  ##STR1375##                                                                             ##STR1376##                                   323                                                                                  ##STR1377##                                                                                  ##STR1378##                                                                             ##STR1379##                                   324                                                                                  ##STR1380##                                                                                  ##STR1381##                                                                             ##STR1382##                                   325                                                                                  ##STR1383##                                                                                  ##STR1384##                                                                             ##STR1385##                                   326                                                                                  ##STR1386##                                                                                  ##STR1387##                                                                             ##STR1388##                                   327                                                                                  ##STR1389##                                                                                  ##STR1390##                                                                             ##STR1391##                                   328                                                                                  ##STR1392##                                                                                  ##STR1393##                                                                             ##STR1394##                                   329                                                                                  ##STR1395##                                                                                  ##STR1396##                                                                             ##STR1397##                                   330                                                                                  ##STR1398##                                                                                  ##STR1399##                                                                             ##STR1400##                                   331                                                                                  ##STR1401##                                                                                  ##STR1402##                                                                             ##STR1403##                                   332                                                                                  ##STR1404##                                                                                  ##STR1405##                                                                             ##STR1406##                                   333                                                                                  ##STR1407##                                                                                  ##STR1408##                                                                             ##STR1409##                                   334                                                                                  ##STR1410##                                                                                  ##STR1411##                                                                             ##STR1412##                                   __________________________________________________________________________    m = n = p = 1                                                                 No.  R          A.sub.1  B.sub.1      A.sub.2                                 __________________________________________________________________________    335  CH.sub.3                                                                                  ##STR1413##                                                                           --                                                                                          ##STR1414##                            336  CH.sub.3 CH.sub.2                                                                         ##STR1415##                                                                           --                                                                                          ##STR1416##                            337  CH.sub.3 CH.sub.2                                                                         ##STR1417##                                                                           --                                                                                          ##STR1418##                            338  CH.sub.3 OCH.sub.2                                                                        ##STR1419##                                                                           --                                                                                          ##STR1420##                            339  n-C.sub.3 H.sub.7                                                                         ##STR1421##                                                                           --                                                                                          ##STR1422##                            340  n-C.sub.5 H.sub.11                                                                        ##STR1423##                                                                           --                                                                                          ##STR1424##                            341  n-C.sub.7 H.sub.15                                                                        ##STR1425##                                                                           --                                                                                          ##STR1426##                            342  CH.sub.2 ═CH                                                                          ##STR1427##                                                                           --                                                                                          ##STR1428##                            343  CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1429##                                                                           --                                                                                          ##STR1430##                            344  CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1431##                                                                           --                                                                                          ##STR1432##                            345  CH.sub.3                                                                                  ##STR1433##                                                                           --                                                                                          ##STR1434##                            346  CH.sub.3 CH.sub.2                                                                         ##STR1435##                                                                           --                                                                                          ##STR1436##                            347  CH.sub.3 CH.sub.2                                                                         ##STR1437##                                                                           --                                                                                          ##STR1438##                            348  CH.sub.3 OCH.sub.2                                                                        ##STR1439##                                                                           --                                                                                          ##STR1440##                            349  n-C.sub.3 H.sub.7                                                                         ##STR1441##                                                                            ##STR1442##                                                                                ##STR1443##                            350  n-C.sub.5 H.sub.11                                                                        ##STR1444##                                                                            ##STR1445##                                                                                ##STR1446##                            351  n-C.sub.7 H.sub.15                                                                        ##STR1447##                                                                            ##STR1448##                                                                                ##STR1449##                            352  CH.sub.2 ═CH                                                                          ##STR1450##                                                                            ##STR1451##                                                                                ##STR1452##                            353  CH.sub.2 ═CH--(CH.sub.2).sub.2                                                        ##STR1453##                                                                            ##STR1454##                                                                                ##STR1455##                            354  CH.sub.2 FCH.sub.2 CH═CH                                                              ##STR1456##                                                                            ##STR1457##                                                                                ##STR1458##                            __________________________________________________________________________    m = n = p = 1                                                                 No. B.sub.2     A.sub.3                                                                              B.sub.3                                                                           A.sub.4                                                                              G                                           __________________________________________________________________________    335                                                                                ##STR1459##                                                                               ##STR1460##                                                                         --                                                                                 ##STR1461##                                                                          ##STR1462##                                336                                                                                ##STR1463##                                                                               ##STR1464##                                                                         --                                                                                 ##STR1465##                                                                          ##STR1466##                                337                                                                                ##STR1467##                                                                               ##STR1468##                                                                         --                                                                                 ##STR1469##                                                                          ##STR1470##                                338                                                                                ##STR1471##                                                                               ##STR1472##                                                                         --                                                                                 ##STR1473##                                                                          ##STR1474##                                339                                                                                ##STR1475##                                                                               ##STR1476##                                                                         --                                                                                 ##STR1477##                                                                          ##STR1478##                                340                                                                                ##STR1479##                                                                               ##STR1480##                                                                         --                                                                                 ##STR1481##                                                                          ##STR1482##                                341                                                                                ##STR1483##                                                                               ##STR1484##                                                                         --                                                                                 ##STR1485##                                                                          ##STR1486##                                342                                                                                ##STR1487##                                                                               ##STR1488##                                                                         --                                                                                 ##STR1489##                                                                          ##STR1490##                                343                                                                                ##STR1491##                                                                               ##STR1492##                                                                         --                                                                                 ##STR1493##                                                                          ##STR1494##                                344                                                                                ##STR1495##                                                                               ##STR1496##                                                                         --                                                                                 ##STR1497##                                                                          ##STR1498##                                345 --                                                                                         ##STR1499##                                                                         --                                                                                 ##STR1500##                                                                          ##STR1501##                                346 --                                                                                         ##STR1502##                                                                         --                                                                                 ##STR1503##                                                                          ##STR1504##                                347 --                                                                                         ##STR1505##                                                                         --                                                                                 ##STR1506##                                                                          ##STR1507##                                348 --                                                                                         ##STR1508##                                                                         --                                                                                 ##STR1509##                                                                          ##STR1510##                                349 --                                                                                         ##STR1511##                                                                         --                                                                                 ##STR1512##                                                                          ##STR1513##                                350 --                                                                                         ##STR1514##                                                                         --                                                                                 ##STR1515##                                                                          ##STR1516##                                351 --                                                                                         ##STR1517##                                                                         --                                                                                 ##STR1518##                                                                          ##STR1519##                                352 --                                                                                         ##STR1520##                                                                         --                                                                                 ##STR1521##                                                                          ##STR1522##                                353 --                                                                                         ##STR1523##                                                                         --                                                                                 ##STR1524##                                                                          ##STR1525##                                354 --                                                                                         ##STR1526##                                                                         --                                                                                 ##STR1527##                                                                          ##STR1528##                                __________________________________________________________________________

EXAMPLE 12 Use Example 1

A nematic liquid crystal composition (hereinafter sometimes referred toas liquid crystal composition A1):

4-(trans-4-propylcyclohexyl)benzonitrile 24% by weight

4-(trans-4-pentylcyclohexyl)benzonitrile 36% by weight

4-(trans-4-heptylcyclohexyl)benzonitrile 25% by weight

4-(trans-4-propylphenyl)benzonitrile 15% by weight had the followingcharacteristics.

Clearing point (Cp): 71.7° C., threshold voltage at a cell thickness of9 μm (V_(th)) 1.78 V, Δε: 11.0, Δn: 0.137, viscosity at 20° C. (η₂₀):27.0 mPa·s

To this liquid crystal composition A1 in an amount of 85% by weight wasmixed 15% by weight of thetrans-4-(trans-4-pentylcyclohexyl)-1-(4-cyano-1-E-butene-3-yne-1-yl)cyclohexane(Compound No. 34) obtained in Example 1 to prepare liquid crystalcomposition B1, and its physical properties were determined to be asfollows:

Clearing point (Cp): 90.0° C., threshold voltage at a cell thickness of9 μm (V_(th)): 1.73 V, Δε: 11.2, Δn: 0.145, viscosity at 20° C. (η₂₀):27.4 mPa·s

While this composition was left in a freezer at -20° C. for 30 days,either separation of crystals and development of smectic phase were notobserved.

EXAMPLE 13 Use Example 2

Liquid crystal composition B2 was prepared in the same manner as inExample 12 with the exception that the4-(trans-4-propylcyclohexyl)-1-(4-cyano-1,3-butadiyne-1-yl)benzene(Compound No. 62) obtained in Example 2 was used instead of the compoundof No. 34, and its physical properties were determined to be as follows:

Clearing point (Cp): 88.4° C., threshold voltage at a cell thickness of9 μm (V_(th)): 1.60 V, Δε: 12.1, Δn: 0.177, viscosity at 20° C. (η₂₀):25.6 mPa·s

While this composition was left in a freezer at -20° C. for 30 days,either separation of crystals and development of smectic phase were notobserved.

EXAMPLE 14 Use Example 3

Liquid crystal composition B3 was prepared in the same manner as inExample 12 with the exception that the compound of No. 246 was usedinstead of the compound of No. 34.

While this composition was left in a freezer at -20° C. for 30 days,either separation of crystals and development of smectic phase were notobserved.

Comparative Example 1

As comparative compound to those of the present invention, compound (a)which is expressed by the formula (13) described above wherein R ispentyl group was actually synthesized, and its physical properties weredetermined in the same manner as in the Examples described above. Theresults were as shown in Table 2 below.

In the Table 2, physical properties of known compounds which areexpressed by the formula (b), (c), or (d) which is the same as theformula (a) described above except that CN group at right side terminalis replaced by Cl, CHF₂, or CF₃, as other comparative compounds; andphysical properties of the compound of No. 34 used in Example 12,compound of No. 62 used in Example 13, and compound of No. 246 used inExample 14 as examples of the compounds of the present invention areshown together.

Among the physical properties, Δε, Δn, and η₂₀ indicate extrapolatedvalues, and physical properties of known compounds expressed by theformulas (a) to (d) are transcribed from those described in theliterature.

                                      TABLE 2                                     __________________________________________________________________________                                     Phase transition                             Compound                         temperature Δε                                                                 Δn                                                                         η20                    __________________________________________________________________________                                                       (mPa.s)                    No. 34                                                                             ##STR1529##                 C.42.8.N.212(dec. >170).I                                                                 12.3                                                                             0.190                                                                            31.9                       No. 62                                                                             ##STR1530##                 C.71.3.N.dec. >150                                                                        24.0                                                                             0.404                                                                            17.7                       No. 246                                                                            ##STR1531##                 C.57.1.N.155.7.I                                                                          16.3                                                                             0.304                                                                            55.3                       (a)                                                                                ##STR1532##                 C.49.7.N.128.9.I                                                                          19.0                                                                             0.224                                                                            13.9                       (b)                                                                                ##STR1533##                 C.66.N.70.I -- -- --                         (c)                                                                                ##STR1534##                 C.37(.N.34).I                                                                             7.8                                                                              0.148                                                                            --                         (d)                                                                                ##STR1535##                 C.108.I     -- 0.169                                                                            --                         __________________________________________________________________________

From the results shown in Table 2, it can be understood that thecompounds of No. 34, No. 62, and No. 246 which are examples of thecompounds of the present invention are equal compared with comparativecompounds expressed by one of the formulas (a) to (d) (comparisonbetween the compound of No. 62 and the compound expressed by the formula(a)), or considerably wide (comparison between the compound of No. 34and the compound expressed by one of the formula (a) to (d)) in thetemperature range in which the compounds exhibit nematic phase;

about the same (comparison between the compound of No. 34 and thecompound expressed by the formula (a)), or considerably large(comparison between the compound of No. 62 and the compound expressed byone of the formulas (a) to (d)) in Δn; and

larger than the compound expressed by the formula (a) which has thelargest value among the comparative compounds in Δε.

Further, as to viscosity (η₂₀), whereas the compounds of the presentinvention exhibit a higher value than that of the comparative compounds,when the viscosity is such an extent, viscosity of liquid crystalcompositions is not so increased even when the compounds of the presentinvention are used as their component, and thus it does not becomespecific problems in actual uses.

As described above, since the compounds of the present invention exhibita large Δn, it is possible to make the thickness of liquid crystal cellssmall by using the compound as component of liquid crystal compositions.Also, liquid crystal compositions having an increased response speedagainst the change in electric field and increased steepness can beobtained by using the present compounds as component since the compoundsof the present invention exhibit a large Δε. Further, when the compoundsof the present invention are used as component of liquid crystalcompositions, the compositions exhibit an excellent miscibility at lowtemperatures. Besides, the present compounds are chemically andphysically stable since they are not decomposed or react with othercomponents.

As described above, liquid crystalline compounds of the presentinvention have a sufficiently large Δn and a large Δε, are excellent inmiscibility with other liquid crystalline compounds, are low inviscosity, and are chemically and physically stable novel liquidcrystalline compounds.

INDUSTRIAL APPLICABILITY

Accordingly, liquid crystal compositions which are improved particularlyin response speed against the change in electric field and steepness,and liquid crystal display devices fabricated by using the liquidcrystal composition can be provided by using the liquid crystallinecompounds of the present invention as component of liquid crystalcompositions.

What is claimed is:
 1. A conjugated nitrile derivative expressed by thegeneral formula (1) ##STR1536## wherein rings A₁, A₂, A₃, and A₄independently represent 1,4-cyclohexylene, 1,4-phenylene in which one ortwo hydrogen atoms on the ring may be replaced by fluorine atom,1,3-dioxane-2,5-diyl, or pyrimidine-2,5-diyl; B₁, B₂, and B₃independently represent a covalent bond, 1,2-ethylene, 1,2-ethenylene,1,2-ethynylene, oxymethylene, methylenoxy, carbonyloxy, or 1,4-butylenegroup; G represents the formula (2), (3), or (4) ##STR1537## Rrepresents an alkyl group having 1 to 10 carbon atoms, a fluoroalkylgroup having 1 to 10 carbon atoms, a halogen atom, or cyano groupprovided that in the alkyl group or fluoroalkyl group, one ornot-adjacent two or more methylene groups or fluoromethylene groups maybe replaced by oxygen atom or 1,2-ethenylene group; and m, n, and p areindependently 0 or
 1. 2. The conjugated nitrile derivative according toclaim 1 wherein m=n=p=0.
 3. The conjugated nitrile derivative accordingto claim 1 wherein m=n=0, and p=1.
 4. The conjugated nitrile derivativeaccording to claim 1 wherein m=0, and n=p=1.
 5. The conjugated nitrilederivative according to claim 1 wherein m=n=p=1.
 6. The conjugatednitrile derivative according to claim 3 wherein G is the group expressedby the formula (2).
 7. The conjugated nitrile derivative according toclaim 6 wherein A₄ is 1,4-cyclohexylene.
 8. The conjugated nitrilederivative according to claim 6 wherein A₄ is 1,4-phenylene ring inwhich one or two hydrogen atoms on the ring may be replaced by fluorineatom.
 9. The conjugated nitrile derivative according to claim 7 whereinA₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.
 10. The conjugatednitrile derivative according to claim 3 wherein G is the group expressedby the formula (3).
 11. The conjugated nitrile derivative according toclaim 10 wherein A₄ is 1,4-cyclohexylene.
 12. The conjugated nitrilederivative according to claim 10 wherein A₄ is 1,4-phenylene ring inwhich one or two hydrogen atoms on the ring may be replaced by fluorineatom.
 13. The conjugated nitrile derivative according to claim 11wherein A₃ is 1,4-cyclohexylene, and B₃ is a covalent bond.
 14. Theconjugated nitrile derivative according to claim 12 wherein A₃ is1,4-cyclohexylene, and B₃ is a covalent bond.
 15. The conjugated nitrilederivative according to claim 3 wherein G is the group expressed by theformula (4).
 16. The conjugated nitrile derivative according to claim 15wherein A₄ is 1,4-cyclohexylene.
 17. The conjugated nitrile derivativeaccording to claim 15 wherein A₄ is 1,4-phenylene ring in which one ortwo hydrogen atoms on the ring may be replaced by fluorine atom.
 18. Theconjugated nitrile derivative according to claim 16 wherein A₃ is1,4-cyclohexylene, and B₃ is a covalent bond.
 19. The conjugated nitrilederivative according to claim 17 wherein A₃ is 1,4-cyclohexylene, and B₃is a covalent bond.
 20. The conjugated nitrile derivative according toclaim 4 wherein G is the group expressed by the formula (2).
 21. Theconjugated nitrile derivative according to claim 20 wherein A₄ is1,4-cyclohexylene.
 22. The conjugated nitrile derivative according toclaim 20 wherein A₄ is 1,4-phenylene ring in which one or two hydrogenatoms on the ring may be replaced by fluorine atom.
 23. The conjugatednitrile derivative according to claim 4 wherein G is the group expressedby the formula (3).
 24. The conjugated nitrile derivative according toclaim 23 wherein A₄ is 1,4-cyclohexylene.
 25. The conjugated nitrilederivative according to claim 23 wherein A₄ is 1,4-phenylene ring inwhich one or two hydrogen atoms on the ring may be replaced by fluorineatom.
 26. The conjugated nitrile derivative according to claim 4 whereinG is the group expressed by the formula (4).
 27. The conjugated nitrilederivative according to claim 26 wherein A₄ is 1,4-cyclohexylene. 28.The conjugated nitrile derivative according to claim 26 wherein A₄ is1,4-phenylene ring in which one or two hydrogen atoms on the ring may bereplaced by fluorine atom.
 29. The conjugated nitrile derivativeaccording to claim 5 wherein G is the group expressed by the formula(2).
 30. The conjugated nitrile derivative according to claim 29 whereinA₄ is 1,4-cyclohexylene.
 31. The conjugated nitrile derivative accordingto claim 29 wherein A₄ is 1,4-phenylene ring in which one or twohydrogen atoms on the ring may be replaced by fluorine atom.
 32. Theconjugated nitrile derivative according to claim 5 wherein G is thegroup expressed by the formula (3).
 33. The conjugated nitrilederivative according to claim 32 wherein A₄ is 1,4-cyclohexylene. 34.The conjugated nitrile derivative according to claim 32 wherein A₄ is1,4-phenylene ring in which one or two hydrogen atoms on the ring may bereplaced by fluorine atom.
 35. The conjugated nitrile derivativeaccording to claim 5 wherein G is the group expressed by the formula(4).
 36. The conjugated nitrile derivative according to claim 35 whereinA₄ is 1,4-cyclohexylene.
 37. The conjugated nitrile derivative accordingto claim 35 wherein A₄ is 1,4-phenylene ring in which one or twohydrogen atoms on the ring may be replaced by fluorine atom.
 38. Aliquid crystal composition comprising at least one conjugated nitrilederivative defined in any one of claims 1 through
 37. 39. A liquidcrystal composition, comprising, as a first component, at least oneconjugated nitrile derivative defined in any one of claims 1 through 37,and comprising, as a second component, at least one compound selectedfrom the group consisting of the compounds expressed by any one of thegeneral formulas (5), (6), and (7) ##STR1538## wherein R₃, Y₁, L₁, L₂,Z₁, and Z₂ may be the same or different from one another among theformulas; R₃ represents an alkyl group having 1 to 10 carbon atoms inwhich alkyl group, one or not-adjacent two or more methylene groups maybe replaced by oxygen atom or --CH═CH--, and any hydrogen atom may bereplaced by fluorine atom; Y₁ represents fluorine atom, chlorine atom,OCF₃, OCF₂ H, CF₃, CF₂ H, CFH₂, OCF₂ CF₂ H, or OCF₂ CFHCF₃ ; L₁ and L₂independently represent hydrogen atom or fluorine atom; Z₁ and Z₂independently represent 1,2-ethylene group, 1,4-butylene group, --COO--,--CF₂ --, --OCF₂ --, --CH═CH--, or a covalent bond; B representstrans-1,4-cyclohexylene, or 1,3-dioxane-2,5-diyl, or 1,4-phenylene inwhich hydrogen atom on the ring may be replaced by fluorine atom; and Crepresents trans-1,4-cyclohexylene, or 1,4-phenylene in which hydrogenatom on the ring may be replaced by fluorine atom.
 40. A liquid crystalcomposition, comprising, as a first component, at least one conjugatednitrile derivative defined in any one of claims 1 through 37, andcomprising, as a second component, at least one compound selected fromthe group consisting of the compounds expressed by the general formula(8) or (9) ##STR1539## wherein R₄ and R₅ independently represent analkyl group having 1 to 10 carbon atoms in which alkyl group, one ornot-adjacent two or more methylene groups may be replaced by oxygen atomor --CH═CH--, and any hydrogen atom may be replaced by fluorine atom; Y₂represents --CN group or --C.tbd.C--CN; E representstrans-1,4-cyclohexylene, 1,4-phenylene, 1,3-dioxane-2,5-diyl, orpyrimidine-2,5-diyl; G represents trans-1,4-cyclohexylene, 1,4-phenylenein which hydrogen atom on the ring may be replaced by fluorine atom, orpyrimidine-2,5-diyl; H represents trans-1,4-cyclohexylene or1,4-phenylene; Z₃ represents 1,2-ethylene group, --COO--, or a covalentbond; L₃, L₄, and L₅ independently represent hydrogen atom and orfluorine atom; b, c, and d are independently 0 or
 1. 41. A liquidcrystal composition, comprising, as a first component, at least oneconjugated nitrile derivative defined in any one of claims 1 through 37,comprising, as a second component, at least one compound selected fromthe group consisting of the compounds expressed by any one of thegeneral formulas (5), (6), and (7) ##STR1540## wherein R₃, Y₁, L₁, L₂,Z₁, and Z₂ may be the same or different from one another among theformulas; R₃ represents an alkyl group having 1 to 10 carbon atoms inwhich alkyl group, one or not-adjacent two or more methylene groups maybe replaced by oxygen atom or --CH═CH--, and any hydrogen atom may bereplaced by fluorine atom; Y₁ represents fluorine atom, chlorine atom,OCF₃, OCF₂ H, CF₃, CF₂ H, CFH₂, OCF₂ CF₂ H, or OCF₂ CFHCF₃ ; L₁ and L₂independently represent hydrogen atom or fluorine atom; Z₁ and Z₂independently represent 1,2-ethylene group, 1,4-butylene group, --COO--,--CF₂ O--, --OCF₂ --, --CH═CH--, or a covalent bond; B representstrans-1,4-cyclohexylene or 1,3-dioxane-2,5-diyl, or 1,4-phenylene inwhich hydrogen atom on the ring may be replaced by fluorine atom; and Crepresents trans-1,4-cyclohexylene, or 1,4-phenylene in which hydrogenatom on the ring may be replaced by fluorine atom, and comprising, as athird component, at least one compound selected from the groupconsisting of the compounds expressed by any one of the general formulas(10), (11), and (12) ##STR1541## wherein R₆, R₇, I, J, and K may be thesame or different from one another among the formulas; R₆ and R₇independently represent an alkyl group having 1 to 10 carbon atoms inwhich alkyl group, one or not-adjacent two or more methylene groups maybe replaced by oxygen atom or --CH═CH--, and any hydrogen atom may bereplaced by fluorine atom; I, J, and K independently representtrans-1,4-cyclohexylene or pyrimidine-2,5-diyl, or 1,4-phenylene inwhich hydrogen atom and on the ring may be replaced by fluorine atom; Z₄and Z₅ independently represent --C.tbd.C--, --COO--, --CH₂ CH₂ --,--CH═CH--, or a covalent bond.
 42. A liquid crystal composition,comprising, as a first component, at least one conjugated nitrilederivative defined in any one of claims 1 through 37, comprising, as asecond component, at least one compound selected from the groupconsisting of the compounds expressed by the general formula (8) or (9)recited in claim 40, and comprising, as a third component, at least onecompound selected from the group consisting of the compounds expressedby any one of the general formulas (10), (11), and (12) recited in claim41.
 43. A liquid crystal composition, comprising, as a first component,at least one conjugated nitrile derivative defined in any one of claims1 through 37, comprising, as a part of a second component, at least onecompound selected from the group consisting of the compounds expressedby any one of the general formulas (5), (6), and (7) recited in claim39, comprising, as another part of the second component, at least onecompound selected from the group consisting of the compounds expressedby the general formula (8) or (9) recited in claim 40, and comprising,as a third component, at least one compound selected from the groupconsisting of the compounds expressed by any one of the general formulas(10), (11), and (12) recited in claim
 41. 44. A liquid crystalcomposition comprising the conjugated nitrile derivative defined inclaim 1 and an optically active compound.
 45. A liquid crystal displaydevice comprising the liquid crystal composition defined in claim 44.